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The American Dream Hit a Wall Starter Homes Are No Longer For nearly a century, the promise of upward mobility in America was tied to one moment: buying your first home. The “starter home” was more than a structure — it was the first rung on the ladder to financial security. But today, in Maryland and across the country, that ladder has splintered. For Gen Z entering the market, the entry-level home is no longer an attainable first step. It’s become a myth from their parents’ generation — a relic of a market that simply doesn’t exist anymore. This episode of Open Floor  began with a conversation you gave at NewDay USA’s headquarters in Fulton, speaking to dozens of young professionals trying to understand a path to ownership that feels closed off to them. What followed was a deep dive into why the “starter home” is collapsing, who’s accelerating its decline, and what solutions actually give future buyers a fighting chance. Why This Matters: The First-Time Buyer Is Disappearing Gen Z staring up an a seemingly impossible wall The core issue isn’t just price. It’s structure — a system that forces young buyers into a game they don’t know the rules to. Most Gen Z buyers: Haven’t been taught financial literacy Don’t understand mortgages or credit-building Lack cash reserves Face wages that haven’t kept pace with rising asset values Are competing directly with institutional investors When you combine this with the volatility of rent, student loans, and high interest rates, Maryland’s first-time buyers are staring at the hardest path to homeownership in modern U.S. history. The numbers confirm it: The median age of a first-time buyer in America is now 38 to 40 years old — an all-time high. That means an entire generation is missing out on 20 years  of potential equity growth. For context?A median Maryland home at $420,000 requires roughly $67,000  upfront to get in the game. Most 23–30-year-olds don’t have that kind of liquidity — and the clock keeps ticking. How Maryland Became Ground Zero for the Affordability Squeeze Maryland’s dynamics are unique: High-wage job corridors (DC–Baltimore Metro) High regulatory barriers Limited developable land Strong buyer demand and low turnover The state needs nearly 600,000 new units  by 2045.Yet most of its metro areas are zoned in ways that restrict exactly the kinds of homes young buyers need most. The result? Maryland is structurally short on supply — and prices behave accordingly. Even counties with relatively lower prices (Somerset, Allegheny, Dorchester) require sacrificing proximity to employment hubs. That means: Longer commutes Less job flexibility Higher transportation costs Reduced economic mobility It’s not just a housing issue — it’s a lifestyle tax. Institutional Investors: Catalyst, Not Cause — But Still a Problem There’s a lot of noise around Wall Street “buying all the homes.” Reality: Institutional investors own less than 1%  of the national housing stock. But here’s what matters: Their purchases are overwhelmingly concentrated in the bottom tier of the market — the starter home segment. That’s the part Gen Z needs most. Academic research shows that when institutional investors enter a market: Starter home prices grow 2.29 percentage points faster Cash offers outmuscle owner-occupants Distressed properties get renovated and marked up Entry-level inventory disappears from reach They’re not causing the shortage — but they’re weaponizing it. The New Barriers for Maryland’s Gen Z Buyers The New Barriers for Maryland’s Gen Z Buyers 1. Lack of credit history, not bad credit - Many young buyers haven’t built enough credit lines to qualify for competitive lending. 2. Misconceptions about down payments - The “20% down” myth is still alive, even though many programs offer 3–5% or specialized grants. 3. Emotional paralysis from rate fear - Buyers wait for rates to drop — but equity doesn’t wait.A $500,000 home today may be $550,000 next year. They lose twice: Higher purchase price Lost year of rent payments 4. Renting is romanticized - Flexibility feels free until buyers realize:Freedom comes from assets, not flexibility. Creative Paths Gen Z Is Taking to Break In A new market requires new strategies: Buying with friends or family House-hacking  (renting rooms) Leveraging occupation-based grants Using community land trusts Seeking entry-level homes in further-out counties It’s not the clean, simple starter home journey of the 1990s. But it’s a way forward. The Real Fix Requires Policy The Real Fix Requires Policy Incremental fixes won’t revive the starter home.The solutions must be structural: Zoning reform - More density, more infill, more multifamily. Land value taxes - Increase the holding cost of unused land to force development. Community land trusts - Separate land from structure to create permanent affordability. Faster permitting and reduced red tape - Make it easier — and faster — to build. This is where federal, state, and local governments must lead. Without deep reform, Maryland risks becoming a state where first-time homeownership is delayed until midlife — or worse, unattainable entirely. The Starter Home Isn’t Just Dying — It’s a Warning The death of the starter home isn’t just a market story. It’s a generational one. If Maryland wants a future where young families can plant roots, build wealth, and create stability, then the state needs bold action — not band-aids. And for the Gen Z buyers fighting their way into the market, the message is simple: the first home doesn’t need to be perfect. It just needs to be yours . Because real freedom — real mobility — starts when you own an asset that grows while you sleep.

From medieval heraldry to modern branding, the Maryland flag tells a story of rebellion, reconciliation, and unrivaled state pride. A Flag That Refuses to Blend In If you live in Maryland, you don’t just fly your flag — you wear  it. It’s on your lacrosse jersey, your truck decal, your porch, your pint glass. The Maryland flag is more than a symbol; it’s a living brand, a visual shorthand for state pride.While most state flags vanish into a sea of forgettable blue seals, Maryland’s doesn’t just stand out — it shouts . Four colors, two family crests, one impossible-to-ignore design. It’s medieval and modern at once, loud and dignified, and instantly recognizable from any distance. Byrd Stadium in College Park, MD - Home of the Maryland Terrapins But the real story isn’t about design at all. It’s about defiance, division, and the brilliance of bringing both sides back together. George Calvert From Rebellion to Refuge: The Vision of George Calvert The Maryland story begins in 17th-century England. George Calvert — the first Baron of Baltimore — was a devout Catholic in a country rapidly turning Protestant and intolerant. Catholics were fined, barred from office, and forbidden from educating their children. So Calvert conceived a radical idea: a New World colony where Christians of all persuasions could worship freely. In 1632, he secured a charter for that dream — the Province of Maryland . When designing its seal, Calvert merged two powerful lineages: the black-and-gold stripes  of his father’s Calvert family and the red-and-white cross  of his mother’s Crossland family. Together, they formed a quartered coat of arms — a balance of paternal strength and maternal heritage. He couldn’t have known it then, but that symbolic marriage would one day become the blueprint for both conflict and unity in his colony’s future. A State Split Down the Middle By the 1860s, Maryland sat on the front line of America’s identity crisis.A slaveholding border state, it was caught between loyalty to the Union and sympathy for the Confederacy. When war came, so did the need for visible allegiance. With no internet, no mass communication, and few newspapers, colors became code — and the ancient Calvert shield became weaponized symbolism. Union loyalists  rallied behind the black and gold  of the Calvert arms — the same colors that once represented colonial authority. Confederate sympathizers  seized upon the red and white  Crossland cross, turning it into an emblem of resistance. Baltimore Riot in 1861 on Pratt Street The same family crest that once united a colony now split a state.Confederate soldiers from Maryland even wore the red cross bottony  on their uniforms — a medieval symbol turned badge of rebellion. Federal troops cracked down, arresting civilians who displayed the red and white. One Union general even joked that if he took the order literally, he’d have to ban peppermint candy and red-haired citizens. It was satire — but not far from the truth. Maryland’s identity was fractured down to its colors. President Lincoln visits soldiers Reconciliation by Design When the Civil War finally ended, Maryland faced a quiet crisis: how to reintegrate thousands of Confederate veterans into a Union state without reopening fresh wounds. The solution came not from legislation or speeches, but from design . Starting in the 1880s, a new symbol began to appear at parades and civic events — a unified flag combining both the black-and-gold Calvert colors and the red-and-white Crossland cross. It was simple but profound: one banner that honored both heritages without glorifying either. In 1888, that same flag flew over Gettysburg , at a ceremony honoring Maryland’s Union soldiers. A symbol once associated with rebellion was now carried proudly beside the colors of the Union — a statement that Maryland’s past would no longer be divided into winners and losers. By 1904 , the Maryland General Assembly made it official: this was the state flag. It wasn’t a symbol of victory. It was a contract of reconciliation. A Crown of Compromise Decades later, Maryland added one final chapter — and it’s pure poetry. In 1945 , a new law required that any ornament atop a Maryland flagpole must be a gold cross bottony  — the same cross once used by Confederate Marylanders. The difference? Now it had to be gold — the Union color. In that one decision, Maryland literally gilded its past: the cross of rebellion crowned in the color of unity.The flag doesn’t erase history. It embodies  it. “The Maryland flag is not a design that hides conflict — it’s one that honors the courage to heal from it.” From Battlefield to Brand Today, the Maryland flag has transcended history to become one of America’s strongest visual brands. At the University of Maryland , the design took on new life through the Maryland Pride  uniforms — a bold collaboration with Under Armour  that turned the flag into high-performance art. The Baltimore Ravens  and Orioles  have embraced it in their gear and stadium design. You’ll even find its patterns etched into microbreweries, surf shops, and boutique apparel lines up and down the Bay. It’s more than nostalgia — it’s cultural code . Every time a Marylander waves that flag, they’re signaling not just where they’re from, but who they’ve chosen to become. Why the Maryland Flag Still Matters Good design tells a story. Great design is  the story.The Maryland flag breaks every rule of vexillology — it’s complex, crowded, and proudly chaotic — but that’s exactly what makes it perfect. Its intricacy mirrors the history it represents: colonial ambition, civil war, reconciliation, and pride. Maryland’s banner doesn’t aim for simplicity; it aims for truth. It’s the only state flag in America that openly celebrates both division and unity — that admits its pain while wearing its pride. And maybe that’s why it endures.Because in every checkered corner and crimson cross, you don’t just see the past — you see the promise of what happens when people refuse to stay divided.

Summer’s surge gave way to balance across Maryland’s markets.From Annapolis to the Shore and beyond, Q3 2025 proved steady, confident, and quietly strong. Overview The third quarter of 2025 brought a soft landing to Maryland’s real estate scene.Sales volume cooled slightly after an energetic first half, yet prices remained steady and demand disciplined.Across the Chesapeake corridor, homes continued moving in weeks—not months—proving that quality and lifestyle still drive the market. Greater Annapolis Pace softened, power held. Homes Sold:  687 (-7 % QoQ) Median Sale Price:  $510 000 (-7.7 % QoQ │ +5 % YoY) Sale-to-List Ratio:  100 % Sales Volume:  ≈ $1.37 B (+6.5 % QoQ │ +16 % YoY) Median DOM:  ≈ 8 days Inventory:  1.9 months Luxury and waterfront listings anchored the quarter. Average luxury sales hit ≈ $1.65 M with a $559 PPSF, underscoring continued appetite for top-tier product.Even with fewer closings, total dollar volume climbed—a clear signal of lasting confidence. Eastern Shore Calm waters. Selective surges. Homes Sold:  459 (-11 % YoY) Median Sale Price:  ≈ $503 K (+1 % YoY) Sale-to-List Ratio:  94 % Sales Volume:  ≈ $103 M (+50 % YoY) Median DOM:  ≈ 16 days Inventory:  4.3 months Buyers chasing tranquility kept the Shore resilient. Waterfront homes averaged $1.59 M ( $480 PPSF ) while luxury sales neared $1.96 M. Fewer listings, same demand: serenity still sells. Greater Baltimore Urban energy, suburban steadiness. Homes Sold:  5 622 (+41 % YoY) Median Sale Price:  $356 000 (+14 % YoY) Sale-to-List Ratio:  100 % Sales Volume:  ≈ $802 M (+64 % YoY) Median DOM:  ≈ 10 days Inventory:  2.3 months From downtown lofts to Howard County estates, liquidity stayed high. Luxury averaged $1.4 M ( $332 PPSF ), moving in ≈ 10 days when priced precisely.Greater Baltimore continues to pair opportunity with balance. Southern Maryland Roots run deep—and confidence deeper. Homes Sold:  1 361 (+37 % YoY) Median Sale Price:  $453 000 (+4 % YoY) Sale-to-List Ratio:  93 % Sales Volume:  ≈ $224 M (+42 % YoY) Median DOM:  ≈ 11 days Inventory:  2.7 months Supply edged upward, but strong fundamentals kept momentum intact. Waterfront averaged $788 K ( $350 PPSF ), and luxury held around $1.22 M. Space, water, and value kept buyers engaged from Solomons to Hughesville. Cross-Market Insights Selective Momentum > Mass Volume  — Intentional buyers define today’s market. Price Integrity Persists  — Stable median pricing signals enduring confidence. Luxury & Waterfront Lead  — High-end performance sets tone for all segments. Days on Market Stay Lean  — Homes continue closing within two weeks region-wide. Closing Thoughts Q3 2025 wasn’t a retreat—it was refinement.Maryland’s markets head into fall with measured strength, low inventory, and resilient demand for lifestyle living. Explore every regional report →   housecats.co/markets | Numbers with soul. Stories that move. Happy hunting.

Check out our episode on the 'Open Floor' Podcast The real estate world just got rocked. Compass, the tech-forward brokerage known for its rapid rise over the last decade, has announced an all-stock acquisition of Anywhere Real Estate — the parent company behind Coldwell Banker, Century 21, Sotheby’s International Realty, Corcoran, ERA, and Better Homes & Gardens Real Estate. This deal, valued at roughly $1.6 billion in equity  and a $10 billion enterprise value  including debt, could create the largest residential brokerage footprint in the world: 340,000 real estate professionals across more than 120 countries and territories. Courtesy of TheRealDeal The Deal at a Glance Structure:  All-stock transaction, valuing Anywhere shares at about $13.01 each . Size:  Combined enterprise value close to $10 billion . Scale:  About 340,000 agents  worldwide under one umbrella. Timing:  Board-approved; closing expected in the second half of 2026 , pending shareholder and regulatory approval. As Barron’s put it, this isn’t just a tuck-in. “This is a tectonic plate shift.” Why Now? The timing is no accident. With high mortgage rates  and tight inventory  squeezing the market, brokers are looking for ways to weather the storm. For Compass, acquiring Anywhere brings: Diversified revenue : franchise royalties, title and escrow, and relocation services. Global brands : Sotheby’s and Corcoran in luxury, Century 21 and Coldwell Banker in mass market. Technology leverage : Compass’s agent platform deployed at massive scale. The thesis is clear: Compass’s technology plus Anywhere’s brands equals an end-to-end engine that could dominate residential real estate. Market Reaction Wall Street’s first impression? Anywhere stock (HOUS):  Jumped more than 50%  on the news. Compass stock (COMP):  Dropped about 12% , reflecting investor concerns over dilution and integration risk. As the saying goes: seller wins now, buyer proves it later. What This Means for Agents For now, Compass has promised brand independence  — Coldwell Banker, Century 21, Sotheby’s, and the rest will keep their names, cultures, and platforms. Still, the merger sets up some major shifts: Compass agents could tap into relocation networks and franchises . Anywhere agents will likely gain Compass’s technology suite  over time. Recruiting wars are heating up, as rivals pitch themselves as “boutique agility” vs. “super-platform scale.” As I said on the podcast: “Giants can’t out-local you. Double down on local expertise and negotiation craft.” What This Means for Consumers Consumers could see: One-stop shopping:  Listing, marketing, title, escrow, relocation under one roof. Private exclusives under a microscope:  Compass pioneered off-MLS “private exclusives,” and a combined giant could put even more emphasis on them. That’s convenience for some, but raises transparency concerns. Fee dynamics:  Consolidation may bring efficiency, but it can also reduce competition. Smart consumers will keep shopping rates and negotiating commissions. Best case? Smoother closings. Worst case? Fewer doors open unless you’re in-network. The Road Ahead for compass The Department of Justice will scrutinize this deal, but with a projected ~25% market share, it’s not technically a monopoly. Still, antitrust concerns, cultural integration, and debt load loom large. Expect: Recruiting battles. Partner renegotiations. More consolidation. If approved, this will be one of the largest brokerage acquisitions of our lifetime  — a move that could forever change how homes are bought and sold. Final Take This is consolidation on a grand scale. Whether you’re an agent, a buyer, or a seller, the Compass–Anywhere deal is something to watch. It could usher in a more integrated, tech-powered real estate experience — or it could concentrate too much power in one super-broker. Either way, the next 12–18 months will be fascinating. What’s your take?  Does a mega-broker make you feel safer or more skeptical? Drop a comment, DM us, or send in a voice memo — we’ll feature the best takes in a follow-up.

M&T Bank Stadium in Baltimore, MD The Chesapeake Bay region is more than history, water, and culture — it’s also home to some of the nation’s most passionate sports communities. From roaring NFL crowds in Baltimore to midshipmen marching in Annapolis, from Big Ten rivalries in College Park to NBA and NHL showdowns just down the road in D.C., professional and collegiate sports here are woven into the fabric of life. Football Powerhouses Baltimore Ravens Baltimore Ravens (NFL)  – Known for the “Ravens Flock,” home games at M&T Bank Stadium create one of the NFL’s most electric atmospheres. Tailgating, purple pride, and rivalries (Steelers, Bengals, Browns) are fall staples. 2025 Baltimore Ravens Home & Away Schedule Week Date Opponent Location Time / Notes 1 Sep 7 @ Buffalo Bills Away – Highmark Stadium 8:20 p.m. ET (Sunday Night) 2 Sep 14 vs Cleveland Browns Home – M&T Bank Stadium 1:00 p.m. ET 3 Sep 22 vs Detroit Lions Home – M&T Bank Stadium 8:15 p.m. ET (Monday Night) 4 Sep 28 @ Kansas City Chiefs Away – Arrowhead Stadium 4:25 p.m. ET 5 Oct 5 vs Houston Texans Home – M&T Bank Stadium 1:00 p.m. ET 6 Oct 12 vs Los Angeles Rams Home – M&T Bank Stadium 1:00 p.m. ET 7 Bye Week — — — 8 Oct 26 vs Chicago Bears Home – M&T Bank Stadium 1:00 p.m. ET 9 Oct 30 @ Miami Dolphins Away – Hard Rock Stadium 8:15 p.m. ET 10 Nov 9 @ Minnesota Vikings Away – U.S. Bank Stadium 1:00 p.m. ET 11 Nov 16 @ Cleveland Browns Away – Cleveland 4:25 p.m. ET 12 Nov 23 vs New York Jets Home – M&T Bank Stadium 1:00 p.m. ET 13 Nov 27 vs Cincinnati Bengals (Thursday Night) Home – M&T Bank Stadium 8:20 p.m. ET (TNF) 14 Dec 7 vs Pittsburgh Steelers Home – M&T Bank Stadium 1:00 p.m. ET 15 Dec 14 @ Cincinnati Bengals Away – Paycor Stadium 1:00 p.m. ET 16 Dec 21 vs New England Patriots Home – M&T Bank Stadium 1:00 p.m. ET 17 Dec 27/28 @ Green Bay Packers Away – Lambeau Field Time TBD 18 Jan 3/4 @ Pittsburgh Steelers Away – Acrisure Stadium Time TBD Jayden Washington Commanders (NFL)  – Based in Landover, MD, the Commanders draw fans from across the DMV. Rivalries with the Cowboys and Eagles make for can’t-miss Sundays. 2025 Washington Commanders Schedule Week Date Opponent Home / Away Time (ET) 1 Sep 7 vs New York Giants Home – Northwest Stadium 1:00 PM 2 Sep 11 @ Green Bay Packers Away 8:15 PM (Prime Video) 3 Sep 21 vs Las Vegas Raiders Home 1:00 PM 4 Sep 28 @ Atlanta Falcons Away 1:00 PM 5 Oct 5 @ Los Angeles Chargers Away 4:25 PM 6 Oct 13 vs Chicago Bears Home 8:15 PM (Monday Night) 7 Oct 19 @ Dallas Cowboys Away 4:25 PM 8 Oct 27 @ Kansas City Chiefs Away 8:15 PM 9 Nov 2 vs Seattle Seahawks Home 8:20 PM 10 Nov 9 vs Detroit Lions Home 4:25 PM 11 Nov 16 @ Miami Dolphins Away 9:30 AM (in Madrid) 12 Bye — — — 13 Nov 30 vs Denver Broncos Home 8:20 PM 14 Dec 7 @ Minnesota Vikings Away 1:00 PM 15 Dec 14 @ New York Giants Away 1:00 PM 16 TBD vs Philadelphia Eagles Home TBD 17 Dec 25 vs Dallas Cowboys Home 1:00 PM 18 TBD @ Philadelphia Eagles Away TBD Navy Midshipmen Football (NCAA, Annapolis)  – College pageantry meets military tradition at Navy–Marine Corps Memorial Stadium. The march-ons, flyovers, and iconic Navy–Air Force clash each October are must-see. Navy Midshipmen 2025 Football Schedule Date Opponent Location Time (ET) Notes Aug 30 VMI Annapolis, MD TBD Season Opener Sep 6 UAB Annapolis, MD 3:30 PM — Sep 13 @ Tulsa Tulsa, OK TBD Conference Game Sep 27 Rice Annapolis, MD 3:30 PM — Oct 4 Air Force Annapolis, MD 12:00 PM Rivalry Game Oct 11 @ Temple Philadelphia, PA TBD — Oct 25 Florida Atlantic Annapolis, MD 3:30 PM Homecoming Nov 1 @ North Texas Denton, TX TBD — Nov 8 @ Notre Dame South Bend, IN 7:30 PM Primetime Game Nov 15 South Florida Annapolis, MD 12:00 PM Senior Day Nov 27 (Thu) @ Memphis Memphis, TN 7:30 PM Thanksgiving Weekend Dec 13 Army (Neutral) Baltimore, MD (M&T Bank Stadium) 3:00 PM Army–Navy Classic Maryland Terrapins Football (NCAA, College Park)  – Competing in the Big Ten, Maryland football Saturdays draw students, alumni, and fans from across the region. Maryland Terrapins 2025 Football Schedule Date Opponent Location Time (ET) Notes / Conference Aug 30 (Sat) vs Florida Atlantic College Park, MD Noon Non-conference Sep 5 (Fri) vs Northern Illinois College Park, MD 7:30 PM Non-conference Sep 13 (Sat) vs Towson College Park, MD Noon Non-conference Sep 20 (Sat) @ Wisconsin Madison, WI Noon Big Ten Oct 4 (Sat) vs Washington College Park, MD 3:30 PM Big Ten Oct 11 (Sat) vs Nebraska College Park, MD TBD Big Ten Oct 18 (Sat) @ UCLA Rose Bowl, CA TBD Big Ten (cross-div) Nov 1 (Sat) vs Indiana College Park, MD TBD Big Ten Nov 8 (Sat) @ Rutgers Piscataway, NJ TBD Big Ten Nov 15 (Sat) @ Illinois Champaign, IL TBD Big Ten Nov 22 (Sat) vs Michigan College Park, MD TBD Big Ten Basketball & Arena Sports Washington Wizards (NBA)  – Just down the road in Washington, D.C., the Wizards draw basketball fans from Maryland and Virginia for regular season and playoff excitement. Washington Capitals (NHL)  – The Caps are known for their dedicated fanbase and Stanley Cup win in 2018. Their home at Capital One Arena is filled with red-clad supporters each fall and winter. Maryland Terrapins Basketball (NCAA)  – Men’s and women’s basketball at UMD are nationally competitive and draw packed crowds at Xfinity Center in College Park. Baseball Traditions Baltimore Orioles (MLB)  – A staple of Charm City, the O’s play at Oriole Park at Camden Yards — widely considered one of the best ballparks in America. The revival of the young roster has reignited fan passion. Washington Nationals (MLB)  – A short trip into D.C., the Nats bring World Series pedigree (2019 champs) and summer-long excitement at Nationals Park. Lacrosse: Maryland’s State Sport PLL (Premier Lacrosse League)  – Founded with deep Maryland roots, PLL showcases pro talent with regular stops in Baltimore. NLL (National Lacrosse League)  – The Baltimore Bayhawks may be gone, but indoor lacrosse still thrives regionally, and the Chesapeake Bay continues to be the heart of lacrosse culture. Maryland Terrapins Lacrosse (NCAA)  – A powerhouse program with multiple NCAA titles, Maryland lacrosse is nationally recognized. Navy Midshipmen Lacrosse  – Annapolis embraces lacrosse each spring with packed stadiums and military pageantry. Beyond the Big Four Soccer:  D.C. United (MLS) and Washington Spirit (NWSL) attract fans from Maryland, with Audi Field in D.C. offering world-class soccer experiences. Citi Tennis & Golf:  The Citi Open (tennis, D.C.) and PGA Tour stops at nearby Congressional Country Club and TPC Potomac showcase elite competition. Specialty Events:  Annual marathons (Baltimore Marathon, Bay Bridge Run), regattas, and sailing competitions blur the lines between sport and lifestyle in this region. Sports as a Way of Life In the Chesapeake Bay region, professional and collegiate sports aren’t just games — they’re cultural anchors. Whether it’s catching a Ravens night game, experiencing the tradition of a Navy football Saturday, or cheering lacrosse at the Xfinity Center, the Chesapeake offers year-round opportunities to connect, celebrate, and belong. Sports here are as much about community and spirit  as they are about competition.

Iconic Professional Tournaments (Worldwide) 1. The Masters (Augusta National Golf Club, GA) Arguably the most prestigious event in golf, The Masters is known for its rich tradition, green jacket ceremony, and the historic setting of Augusta National. Played every April, it’s the first major championship of the year and a must-watch for golf fans. 2. U.S. Open (Various Locations) One of the four major championships, the U.S. Open is famous for its brutally challenging setups and historic venues. It’s where legends are made—and broken. 3. The Open Championship (UK) Often referred to as “The British Open,” this is the oldest major championship in golf. Held on coastal links courses throughout the UK, it’s known for unpredictable weather and deep-rooted traditions. 4. PGA Championship (Various Locations) The final major of the season, this event typically draws the deepest field and showcases both veteran champions and emerging stars. 5. Ryder Cup (USA vs. Europe, Alternating Host) Held every two years, this team event pits the best golfers from the U.S. against those from Europe in a match-play format filled with passion, pressure, and patriotism. Premier Professional Golf in Maryland 1. BMW Championship at Caves Valley Golf Club (2021) Caves Valley, one of Maryland’s premier clubs, hosted the BMW Championship —a FedExCup Playoff event—bringing the PGA Tour’s best to Owings Mills. The event was a massive success and helped raise Maryland’s profile as a competitive golf destination. 2. LPGA Championships at Bulle Rock (2005–2009) Bulle Rock Golf Club in Havre de Grace hosted the LPGA Championship , a women’s major, for five consecutive years. Winners like Annika Sörenstam and Yani Tseng contributed to the course’s growing reputation. 3. Middle Atlantic PGA Section Championships Held at rotating venues throughout Maryland and nearby states, this regional professional event showcases top club professionals and aspiring tour players. Regional and Community Events in Maryland 1. Chesapeake Cup at Queenstown Harbor One of the most anticipated public course tournaments in the region, the Chesapeake Cup features top amateur players from across the Eastern Shore competing in a scenic, competitive environment. 2. Club Championships (Various Clubs) Private clubs like Chartwell , Crofton , Baltimore Country Club , and Talbot Country Club host annual Club Championships . Members compete for bragging rights and trophies across multiple flights. 3. Member-Guest Invitationals A staple at private clubs across the state, Member-Guest Tournaments are equal parts social and competitive. These multi-day events often include pairing parties, match play rounds, and formal dinners. Standout examples include those at South River , Swan Point , and Hobbit’s Glen . 4. Charity and Fundraising Events Many Maryland clubs host high-impact charity tournaments throughout the year. Notable events include: First Tee of Greater Baltimore Fundraiser Wounded Warrior Golf Classic (Anne Arundel County) Boys & Girls Club of Annapolis Charity Golf Outing These events bring together local businesses, community leaders, and passionate golfers in support of meaningful causes. Amateur Competitions Worth Following 1. Maryland Open Hosted by the Maryland State Golf Association (MSGA) , this is the premier state-level championship for amateurs and professionals. It rotates among the state’s top courses and always draws a strong field. 2. Maryland Amateur & Mid-Amateur Championships These highly competitive events highlight Maryland’s best amateur players, typically held at premier private clubs. 3. U.S. Open Local Qualifiers Held annually at clubs like Woodholme and Turf Valley , these qualifiers are stepping stones for golfers with dreams of competing on the biggest stage. The Experience of Golf in Maryland Golf in Maryland is more than just a game; it’s a lifestyle. The thrill of competition, the beauty of the courses, and the camaraderie among players create an unforgettable experience. Whether you’re a seasoned pro or just starting out, there’s something for everyone. Imagine standing on the lush greens of a prestigious course, the sun shining down as you prepare for your next swing. The excitement in the air is palpable. You’re not just playing; you’re part of a community that shares your passion. Why Golf Matters Golf is a sport that transcends age and skill level. It’s about connection—connecting with nature, with friends, and with the game itself. In Maryland, the golf scene is vibrant and welcoming. From professional tournaments to local charity events, there’s always something happening. Final Thoughts From the polished greens of Augusta to local showdowns on the Chesapeake, golf competitions create moments that define careers—and communities. Whether you're chasing a club title, watching the world’s best compete, or swinging for charity, Maryland’s tournament scene is rich with opportunity and tradition. It's not just about the score; it's about the experience. So, grab your clubs and get ready to tee off. The world of golf awaits you! ---wix---

Greater Annapolis – Resilient Demand Amid Low Supply Greater Annapolis (Anne Arundel County) remains a standout market as we head into fall 2025. Recent data show that home sales have held steady  – about 744 homes sold in July 2025 , roughly on par with the same month last year (+0.8% year-over-year). Prices continue to climb  modestly, with the median sale price around $505,000  (up ~4.1% from July 2024). This price growth, despite higher interest rates, underscores the persistent demand in the area. Inventory, however, remains extremely tight . Anne Arundel County has only about 1.9 months of housing supply , keeping it firmly in a seller’s market  (far below the ~6 months needed for a balanced market). Even though homes aren’t selling at the lightning pace of last year’s frenzy, they are still moving quickly  – the median time on market in July was just 9 days , up from 6 days last year but still under two weeks . Buyers are out there and acting fast  on desirable listings, often yielding sale-to-list price ratios at or near 100%. What’s driving this resilience in Greater Annapolis? A combination of factors: strong local demand , limited new inventory, and the area’s enduring appeal (from waterfront properties to convenient commutes). In July, the market saw activity across price points – including 42 waterfront homes  and 65 luxury homes  sold that month  – indicating that even higher-end segments are seeing movement. Entry-level and mid-range homes, however, are the hottest commodities, as first-time buyers and move-up buyers compete for the few available options. All signs point to Annapolis staying competitive  this fall, with well-priced homes continuing to draw interest soon after listing. “When homes take longer to sell, it signals a more deliberate buyer environment, and that’s what we’re seeing today. Affordability remains a top issue.”  – Cheryl Abrams Davis, 2025 President of Maryland REALTORS® thebaynet.com This more measured pace in Annapolis doesn’t mean a lack of demand – it means buyers are being strategic and price-conscious . Sellers still have the advantage given low supply, but they must align with the market on pricing and condition  to attract today’s more cautious buyers. Properly priced, move-in-ready homes in Annapolis are still receiving multiple offers  and can sell quickly, whereas overpricing may lead to longer time on market. The quote above highlights that buyers are taking their time and weighing affordability , a trend we’re noticing locally as higher mortgage rates have curbed some of the urgency. In short: Greater Annapolis enters the fall with a healthy market, albeit one that’s normalizing from the craze of the past few years.   🎯 Key takeaway:  Sellers should remain confident but realistic, and buyers who are prepared can still secure a home in this coveted area without the extreme bidding wars of 2021–2022. Regional Market Highlights – Other Areas at a Glance While Greater Annapolis is our cornerstone, it’s insightful to see how other nearby Maryland markets are performing as we approach fall. Here’s a quick rundown of regional trends , showing both similarities and contrasts: Southern Maryland (Calvert, Charles & St. Mary’s Counties):  This region continues to see steady growth . July sales were up ~3.7% year-over-year , and median prices rose about 4.8%  vs. last year . With a median sale around the mid-$400Ks, Southern Maryland remains relatively affordable and in demand. Inventory sits at roughly 2.6 months  (a seller’s market), and homes spent a median of 13 days on market (up from 11 days last year) . The combination of suburban appeal and value (especially for buyers commuting to D.C. or Andrews/Pax River) keeps this market active , though buyers are negotiating a bit more than last year. Eastern Shore (Queen Anne’s, Kent & Talbot Counties):  The Eastern Shore market has cooled to a balanced condition  after the pandemic-era rush on rural and waterfront properties. July sales were up a slight 3.4%  year-over-year, but notably prices dipped  – median sale price was about 4% lower than a year ago . This hints at some normalization (perhaps fewer high-end sales than last summer). Inventory is around 4 months , which is right on the cusp of a balanced market . In other words, supply and demand are more in equilibrium here than in other regions. Homes are spending longer on the market (median 18 days, vs 11 days last year) as buyers have more choices . Well-priced waterfront and vacation homes will still attract interest, but generally buyers have the breathing room to be selective  on the Eastern Shore this fall. Greater Baltimore (Baltimore City, Baltimore County, & Howard County):  The metro Baltimore area is showing mixed signals . Sales volumes in July were down about 5% from last year  (1,679 homes vs ~1,902 in July 2024), yet prices have climbed  – median sale price jumped roughly 8% year-over-year . This implies that while fewer homes are changing hands (likely due to limited inventory and some buyer fatigue), the properties that do sell are still fetching higher prices. Inventory in Greater Baltimore remains low at around 2.4 months  of supply . keeping it a seller’s market . However, the median days on market rose to 13 days  (from just 9 days last year), another sign that buyers are no longer rushing en masse . Popular suburban spots (like Howard County or northern Baltimore County) continue to see competition for turnkey homes, whereas in the city and higher price tiers, sellers are having to work a bit harder (and price more keenly)  to get deals done. Across all these regions, a common thread is that housing supply is still historically low  – but demand has become more measured compared to the frenzied market of a couple years ago. Prices are generally holding or rising  year-over-year in most markets, a testament to that low supply, even as sales volumes have dipped  in some areas. Buyers today are contending with higher monthly payments due to interest rates, so they’re laser-focused on value, which leads to slightly longer sales timelines and more negotiation  in many cases. Sellers around Maryland are noticing this shift. In fact, Maryland’s statewide July housing stats showed sales down 9.6% from a year ago , even as the median price inched up 2.8%  to $445, 000 . Active listings have ticked up slightly (+0.5% year-over-year statewide), and Maryland now has about 2.6 months of inventory  – still well below a balanced level, but higher than the ultra-tight conditions we saw in 2022 . Homes are taking longer to sell  on average (median 13 days on market versus just 8 days last summer), reflecting this more patient market environment. Economic Factors Shaping the Market Several economic factors  and major news stories  are influencing buyer and seller behavior in late 2025: Mortgage Rates & Affordability Mortgage Rates & Affordability:  Mortgage interest rates have been hovering in the 6%–7% range  for most of the past year . The Federal Reserve kept its benchmark rate unchanged at the June meeting, and while some forecasts predict a modest rate cut in 2025, no significant relief is expected in the immediate term . These higher borrowing costs directly impact affordability – even though prices aren’t surging like before, the cost of financing a home is substantially greater  than a few years ago. As a result, monthly payments for a median-priced home in Maryland are straining budgets, and some would-be buyers have held off  or exited contracts upon realizing the payment burden . The uptick in deal cancellations  is one sign: about 13.2% of pending sales in the Baltimore metro fell through in June 2025 , the highest June cancellation rate in recent history . High prices coupled with high rates are causing buyers to be more cautious, and in some cases, back out if inspections reveal costly issues or if a better home hits the market . Local Economy & Employment Local Economy & Employment:  On the positive side, Maryland’s job market has remained relatively stable, and sectors like government, defense, and healthcare provide a steady stream of buyers (and some incoming residents). We haven’t seen major layoffs regionally that would flood the market with listings; rather, the bigger issue is homeowners staying put . Many potential sellers refinanced or bought when rates were 3%, and are reluctant to give up their low-rate mortgages, contributing to the inventory shortage . This “lock-in effect” means fewer move-up buyers listing homes, which in turn restricts choices for first-time buyers. The stalemate continues: people who might want  to move are weighing the cost of financing their next home and often deciding to renovate or stay put  instead. This has kept resale listings scarce across Anne Arundel and surrounding counties. Housing Policy & Supply Constraints Housing Policy & Supply Constraints:  A major story impacting the housing market is the ongoing shortage of affordable housing  in Maryland. A recent report from the University of Maryland’s National Center for Smart Growth estimates the state faces a deficit of nearly 300,000 affordable housing units . This shortfall disproportionately affects those with moderate or fixed incomes and puts pressure on the entire market (as many buyers are pushed into competing for market-rate homes). Industry leaders are vocal about this issue. Cheryl Abrams Davis (Maryland REALTORS® President) has criticized local governments for zoning and development constraints, arguing that without more “middle housing” (like townhomes, duplexes, ADUs) and affordable options, young professionals, working families, and downsizing seniors have nowhere to go . She warns that if local authorities don’t act, “economic vitality will suffer as buyers look for more affordable homes outside this great state”. This backdrop of high demand and low supply  is the fundamental economic driver of our housing market conditions – it’s why prices remain elevated and why any relief in competition tends to be modest. Until we see changes like increased new construction, zoning reform, or infrastructure that opens new areas for development , the Maryland housing market is likely to stay tighter than buyers would prefer. Regional Developments Regional Developments:  Regionally, there are a few bright spots and challenges worth noting. Large employers in the Baltimore–Washington corridor continue to hire (or at least backfill positions), which sustains housing demand. We’re also seeing infrastructure improvements  (for instance, ongoing discussions about a new Chesapeake Bay crossing and local highway upgrades) which, if realized, could expand the radius of feasible commutes and unlock new housing growth in coming years. On the flip side, insurance and climate concerns  are creeping into real estate decisions – waterfront communities around the Chesapeake are increasingly mindful of flood insurance costs and climate resiliency, although this has not yet significantly dampened demand for those coveted locations. These factors haven’t dramatically altered the fall market, but they add context: buyers and sellers are planning for the long term , considering not just interest rates and prices, but also where the region is headed in terms of growth and livability. In summary, the economic picture as we enter fall is one of moderating activity underpinned by solid fundamentals . Higher financing costs  have cooled the pace from the ultra-hot market of 2021, but low inventory and a strong local economy  mean we are far from any downturn in home values. Instead, we have a market that’s seeking equilibrium  – and gradually finding it as both sides adjust expectations. Fall 2025 Outlook – Opportunities, Trends & Fast-Moving Properties As the busy summer real estate season winds down, what can buyers and sellers expect this fall? Historically, autumn brings a slower tempo : there are usually fewer buyers actively house-hunting (many families prefer to move before the new school year), and inventory often peaks in late summer then declines. However, fall 2025 is shaping up to offer some unique opportunities  – and certain properties will continue to move quickly even in the cooler months. Let’s break down the key fall trends: 1. More Choices for Buyers (and More Time to Decide):  This fall could be a bit of a “sweet spot” for buyers.  The frantic competition of spring has eased, and inventory levels are actually higher than we’ve seen in recent years. Zillow data shows the number of homes on the market nationally is the highest since mid-2020 , thanks to a buildup of listings that didn’t sell over the summer . In fact, the past two years saw peak inventory in October , and 2025 looks to repeat that pattern. New listings trickled in during late summer and early fall, but many spring listings have lingered unsold , meaning buyers now have a wider selection  – **20% more homes for sale nationally than a year ago, as of mid-year . Fewer active buyers also mean you’re less likely to get into a bidding war this season. Kara Ng, a senior economist at Zillow, notes that a lot of house hunters are in “wait-and-see” mode: “There’s a lot of uncertainty out there, and some buyers are just waiting to see what happens. So if you’re able to buy, fall could be a sweet spot since you won’t be competing against the pool of buyers waiting on the sidelines.” In practical terms, buyers can afford to be a bit more deliberate . Homes aren’t flying off the shelf in mere days like before; you might have a few weeks to house-hunt and compare options  rather than a few days. For example, last year it took on average 17 days longer for a typical U.S. home to go under contract in November vs. May . We expect a similar dynamic this year – the pace is “far from leisurely,” but definitely less frantic , giving buyers breathing room to consider inspections, weigh their budget, and make contingency-inclusive offers  without immediately losing out. 2. Prices Leveling Off (and Even Softening in Spots):  After years of double-digit appreciation in home values, price growth has flattened  in many markets. We’re not seeing widespread price drops in Maryland, but sellers have become more realistic. Many listings are now adjusting prices or offering concessions  if they don’t get traction in the first few weeks. In fact, last fall saw the highest rate of price cuts in September and October , and we anticipate a similar or higher rate this fall . Already by May 2025, 26% of U.S. listings had a price reduction  – a sign that sellers are responding to the cooler demand . Zillow’s economists predict a slight decline (around 1–1.5%) in national home values by the end of 2025 . Locally, that could translate to essentially flat prices through the rest of the year  (some neighborhoods might see minor dips, especially where prices overshot affordability). For buyers, this is encouraging: the era of rushing to offer over-asking is fading. You may even negotiate sales prices below list  in certain cases – something virtually unheard of during the 2021 boom. (In Greater Annapolis, for instance, homes have recently sold for an average of about 1% below asking  as negotiations normalize .) Importantly, lower prices are not forecast in a dramatic way , but this flattening trend gives buyers a chance at a better deal  or at least the peace of mind that they’re not chasing a rapidly rising target. Sellers should note that while demand is still out there, overpricing a home this fall is likely to backfire  – today’s buyers will pass on a listing that doesn’t compare well on value, and it could stagnate until a price cut is made. The silver lining for sellers is that if you price appropriately from the start, you can still sell at a very strong price point , given that overall inventory is low by historical standards. 3. Stable (but High) Mortgage Rates – Plan Accordingly:  As mentioned earlier, mortgage rates are expected to hold in the high-6% range  through the fall . There’s always a possibility of economic news pushing them slightly up or down, but no significant relief is likely in the immediate weeks. Buyers should lock in a rate  when they see a favorable dip and budget conservatively . The good news is, with rates having been elevated all year, lenders have gotten creative  – we’re seeing more offers of rate buydowns, adjustable-rate mortgages (ARMs) , and other financing incentives. Some sellers (and new home builders) are even offering to cover closing costs or buy down the buyer’s rate for the first couple of years . These concessions can make a big difference in affordability. If rates do unexpectedly dip late in the year, buyers who locked in can always refinance; if they rise, those who secured today’s rate will be glad they did. For now, the environment of rate stability means buyers can calculate their budget with more certainty  – there’s less fear of being priced out by a sudden rate spike. However, it also means there’s no sense in waiting for dramatically lower rates  before buying; sitting on the sidelines could just mean paying more for the house itself if prices tick up next spring. Each buyer’s situation is unique, but generally fall buyers can proceed knowing what they’re dealing with in terms of financing costs , and that predictability is valuable. 4. Sellers: ‘Tis the Season to Motivate (Staging & Incentives Matter):  Fall historically brings out the most motivated sellers . If someone lists their home in October or November, they usually need  to sell (job relocation, already bought another home, etc.), which means opportunity for buyers. Already we’re hearing of more seller incentives  – from home warranties, to covering transfer taxes, to outright price cuts – to get deals done . Sellers who are successful this fall will likely be those who price correctly from the outset  and perhaps sweeten the deal (e.g. including some furniture, offering a credit for new appliances, or being flexible with closing timelines). Also, presentation is key : as the weather cools, homes with “cozy” appeal tend to shine . Properties featuring fireplaces, updated heating systems, warm lighting and tasteful autumn décor can emotionally resonate with fall buyers . Many buyers envision spending the upcoming holidays in their new home, so staging a home to feel inviting this time of year can give sellers an edge. Curb appeal also shifts in the fall – well-maintained yards with autumn flowers or foliage , clean gutters, and seasonal decorations (kept moderate and tasteful) can make a home stand out. The bottom line for sellers is that the pool of buyers may be smaller now, but they are serious  – so capturing their interest through proper pricing and presentation is crucial. A seller might not get 10 offers like in spring, but getting one solid offer in fall  is absolutely achievable if the home is marketed well. In fact, homes that check all the right boxes (great location, move-in ready, and priced right) can still ignite competition. Our local data shows that “hot” listings – those that are turnkey and hit a sweet spot in pricing – can go under contract in around 2 weeks, sometimes at or above asking price . So, there is still a fast lane  in the fall market for the best properties. 5. Which Properties Will Move Fast in Fall?  Generally, we expect smaller, affordable homes and any highly updated property  to be among the quickest to sell this fall. Why? The entry-level segment  remains underserved – many renters and first-time buyers are still eager to purchase if they find a home within their budget. Thus, a well-priced townhome, condo, or starter single-family home in Anne Arundel or surrounding areas may still see strong competition and multiple offers  even in October or November. Additionally, homes that cater to downsizers or retirees  (think one-level living, low maintenance) could move swiftly; many older buyers don’t time moves around school schedules and will act when the right home appears. We also see continued demand for homes with unique features  like water views or large lots – those niche buyers are always watching, and if inventory in that category has been thin, a new listing can attract quick interest regardless of season. To drive a quick sale in fall, pricing is paramount . Buyers have more confidence to walk away or wait for price drops  now, so the homes that sell fastest will be those that are clearly a good value  in their segment. Lastly, it’s worth noting that move-in-ready condition  is a huge plus as the year winds down. Many buyers aiming to move in fall want to be settled before the holidays and cold weather, and they may not have the appetite for significant renovations. A home that is clean, repaired, and comes with recent updates (or perhaps comes furnished or with big-ticket items like the hot tub or playset included ) can entice buyers to act quickly, knowing they can transition smoothly  into their new space. In essence, the fall 2025 market offers a breather  for buyers and an end-of-year window for sellers to make deals – but it’s by no means idle. We anticipate a healthy churn of sales through September, October, and early November , especially for those prime properties and eager buyers who sat out the summer. The market sentiment is cautiously optimistic: buyers are gaining a bit of power back , yet sellers who adapt to the new normal are still achieving excellent prices. Keep an eye on interest rates and new listings in your target area; an unexpected dip in rates or a late flood of listings could spur a burst of activity. But barring surprises, expect a steadier, more methodical real estate season . For buyers, this is the time to capitalize on negotiability and choice , and for sellers, it’s an opportunity to shine by being the best value on the block . Sources: Housecats Real Estate Market Reports – Greater Annapolis, Southern MD, Eastern Shore, Greater Baltimore (July 2025 data) housecats.co . These reports provide recent sales trends, prices, and inventory indicators for our local markets. Maryland REALTORS® Housing Statistics – July 2025 Press Release thebaynet.com . Statewide perspective on sales volume, price changes, inventory and quotes on market conditions. The BayNet / Maryland REALTORS®  – Commentary from Maryland REALTORS® President on the current market and housing supply issues thebaynet.com . Patch (Annapolis)  – Housing Market Cooling  (July 2025) patch.com . Insight on rising contract cancellation rates and buyer sentiment from Redfin analysis. Zillow Research  – Fall 2025 Market Outlook zillow.com . Analysis of seasonal trends (inventory, pricing, and buyer behavior) suggesting fall advantages for buyers and flattening prices. Redfin Housing Data (Annapolis)  – Market competitiveness metrics (days on market, sale-to-list ratios, etc.) redfin.com , illustrating how “hot homes” are still selling quickly with multiple offers. Local Agent Perspective  – Fall real estate trends (Sneffels Realty, 2025) ridgwaycorealestate.com , highlighting what features attract buyers in cooler seasons and how sellers can appeal to fall buyers.

Fall in the Chesapeake Bay region is more than golden leaves and cooler breezes — it’s a season of celebration. Every weekend brings something new: schooners racing across the Bay, midshipmen marching into Navy–Marine Corps Memorial Stadium, Renaissance villagers filling the woods of Crownsville, and neighborhoods lighting up with lantern parades. From Annapolis to Easton, Baltimore to Southern Maryland, communities gather to honor history, cheer their teams, and embrace the rhythm of the season. Greater Annapolis & Anne Arundel County The Annapolis area hosts a mix of cultural, artistic, and maritime events each fall. Major 2025 highlights include: Maryland Renaissance Festival Maryland Renaissance Festival (Crownsville)  – Runs weekends from late August through October 19, 2025, transforming a wooded village into a 16th-century celebration of merriment. Jousting knights, costumed performers, artisans, and live music draw crowds throughout its run, making “Renn Fest” a beloved annual tradition. Kunta Kinte Heritage Festival (Annapolis) Kunta Kinte Heritage Festival (Annapolis)  – On September 13, 2025, the 35th annual Kunta Kinte festival will celebrate African American heritage with a full day of music (R&B, gospel, jazz, reggae and more), dance, cultural exhibits and family activities . Known as one of the East Coast’s largest African American cultural festivals, it attracts thousands to honor the legacy of Kunta Kinte and the African diaspora. Annapolis Songwriters Festival   Annapolis Songwriters Festival  – September 11–14, 2025, downtown Annapolis’s pubs and theaters come alive with intimate acoustic performances . Modeled after the famed Key West festival, it features singer-songwriters sharing stories behind their songs in historic venues, creating a soulful atmosphere that earned rave reviews in its debut years . Annapolis Baygrass Music Festival   Annapolis Baygrass Music Festival  – September 20–21, 2025, a waterfront bluegrass and Americana festival that blends music with environmental awareness . Held on a Chesapeake beachfront, attendees enjoy national and regional jam-grass acts plus yoga, workshops, and bay conservation activities by day. It’s a “music meets nature”  experience that has quickly become a regional favorite . United States Powerboat & Sailboat Shows (Annapolis) United States Powerboat & Sailboat Shows (Annapolis)  – Oct 2–5 (Powerboat) and Oct 9–12 (Sailboat) in 2025. These back-to-back international boat shows turn Annapolis Harbor into a sea of masts and gleaming yachts, attracting tens of thousands of boating enthusiasts . Attendees can board new boat models, check out marine gear, and enjoy nautical culture in the “Sailing Capital” of the U.S. Navy Football Home Games (Annapolis) Navy Football Home Games (Annapolis)  – Throughout fall 2025 (August–November), Navy–Marine Corps Memorial Stadium buzzes with pageantry each home game weekend . The U.S. Naval Academy’s football games (including the Navy vs. Air Force  clash in early October) draw capacity crowds, with midshipmen march-ons and a festive citywide atmosphere – Annapolis swells with visiting fans and school spirit on game days . 2025 Navy Home Football Games in Annapolis: August 30: vs. VMI  September 6: vs. UAB  September 27: vs. Rice  October 4: vs. Air Force  October 25: vs. Florida Atlantic (Homecoming)  November 15: vs. USF  Chesapeake Bay Bridge Run Chesapeake Bay Bridge Run  – On November 9, 2025, the Bay Bridge 10K run/walk offers a rare chance to traverse the 4.3-mile Chesapeake Bay Bridge on foot. This popular race (open to runners and walkers) provides “expansive”  Bay vistas from 186 feet up, minus any vehicles – a bucket-list experience that sells out annually. Annapolis Jazz & Roots Festival Annapolis Jazz & Roots Festival  – November 7–16, 2025, a multi-venue music festival showcasing jazz, blues, and folk roots across Annapolis and Eastport. In its 4th year, most events are free (with a couple ticketed shows), highlighting both world-renowned and hometown Maryland artists . With performances in art galleries, libraries, churches and clubs, it’s a growing fall tradition supported by local arts councils . Eastern Shore (Maryland) The Eastern Shore’s fall events celebrate the region’s unique heritage – from folk culture to maritime traditions and wildlife art. Notable fall 2025 events: Maryland Folk Festival (Salisbury) Maryland Folk Festival (Salisbury)  – Sept 19–21, 2025, a free  three-day festival of traditional music, dance, stories and arts from across America . This is the 3rd annual Maryland Folk Festival (born from Salisbury’s stint hosting the National Folk Festival), and it will feature dozens of performances on multiple stages plus craftspeople, food vendors and participatory workshops, all celebrating diverse cultural traditions . IRONMAN Maryland Triathlon (Cambridge) IRONMAN Maryland Triathlon (Cambridge)  – Sept 20, 2025. An elite endurance race in and around the Choptank River, where athletes from around the world tackle a 2.4-mile swim, 112-mile bike, and 26.2-mile run. Cambridge’s flat courses and enthusiastic community support make this one of the most popular full IRONMAN events on the East Coast , drawing competitors and spectators for a weekend of athletic achievement. Sultana Downrigging Festival (Chestertown)   Sultana Downrigging Festival (Chestertown)  – Oct 31–Nov 2, 2025. One of North America’s largest annual tall ship gatherings , Downrigging Weekend turns historic Chestertown into a nautical celebration. Dozens of majestic schooners and wooden ships offer public sails and deck tours by day, while bluegrass concerts, waterfront fireworks, and educational exhibits fill the town. It’s a hands-on homage to maritime history that has become a Kent County signature event. Easton Waterfowl Festival   Easton Waterfowl Festival  – Nov 14–16, 2025, Easton, MD’s famed wildlife art and heritage festival now in its 54th year . Over three days, 25,000+ visitors enjoy world-class decoy carving and painting exhibits, a conservation-focused art auction, retriever dog demonstrations, calling contests, and country/folk music shows . The festival’s proceeds support habitat conservation – more than $5.7 million  raised over its history – making this a feel-good and fun community tradition . Also noteworthy: the Eastern Shore hosts many local fall fairs and outdoor events, from classic car shows to oyster roast fundraisers. For instance, the Concours d’Elegance  on Kent Island each September showcases rare classic automobiles in a waterfront setting, and the Mid-Atlantic Small Craft Festival  (Oct 2025 in St. Michaels) celebrates traditional boatbuilding. However, the above events are among the region’s largest and most popular. Southern Maryland (Calvert, Charles & St. Mary’s Counties) Southern Maryland’s fall happenings showcase its watermen heritage, rural culture, and community spirit: Washington Commanders home games Washington Commanders (Landover, Prince George’s County)  – Just up the road from Southern Maryland, Commanders games at Commanders Field  (formerly FedExField) are a fall staple for NFL fans. Home Sundays (September–December 2025) bring tailgates, marching bands, and divisional rivalries that light up the stadium. The venue draws fans from across D.C., Maryland, and Virginia, making it one of the region’s biggest sporting gatherings each autumn. 2025 Washington Commanders Home Games (Landover, MD): September 7: vs. Philadelphia Eagles September 21: vs. Dallas Cowboys October 5: vs. New York Giants October 19: vs. Green Bay Packers November 2: vs. Chicago Bears November 23: vs. Pittsburgh Steelers December 7: vs. Tampa Bay Buccaneers Blessing of the Fleet (St. Mary’s County) Blessing of the Fleet (St. Mary’s County)  – Oct 4, 2025. A cherished tradition since 1967, this event blesses the local fishing fleet and celebrates St. Mary’s County’s heritage . Now held at Leonardtown Wharf , the family-friendly festival features live music, colonial reenactors, kids’ activities, local seafood and craft vendors, and even fireworks. It’s a day of community pride honoring the region’s watermen and historic beginnings (the blessing commemorates the 1634 landing of the Maryland colonists). Patuxent River Appreciation Day (Solomons)   Patuxent River Appreciation Day (Solomons)  – Oct 11, 2025 at Calvert Marine Museum. Known as “PRAD” , this free waterfront festival highlights the Patuxent River’s natural and cultural importance . Visitors can enjoy boat rides, environmental exhibits, live island/bluegrass music, an arts & crafts fair, local food, and children’s activities. It’s a well-loved annual event (40+ years running) that brings together local businesses, conservation groups and families to “appreciate” Southern Maryland’s defining river . St. Mary’s County Fair (Leonardtown)   St. Mary’s County Fair (Leonardtown)  – Sept 18–21, 2025. A classic county fair dating back generations , featuring 4-H livestock shows, home arts exhibits, carnival rides, tractor pulls and live entertainment. From prize-winning pumpkins to pig races, this fair offers an authentic slice of Southern Maryland life. It consistently earns praise as a friendly, well-run fair where the community comes together to celebrate its agricultural roots each fall. Greater Baltimore Area Baltimore’s fall calendar is packed with festivals and big events reflecting the city’s arts, sports, and historic culture: Baltimore Book Festival   Baltimore Book Festival  – Sept 13–14, 2025. The city’s premier literary festival (now in its 26th year) returns to the Waverly neighborhood with 80+ featured authors and a full schedule of talks, panels, poetry readings and workshops . The free, family-friendly festival brings bibliophiles together for two days of “where words take center stage,”  complete with book signings, a booksellers’ marketplace, live music, children’s storytimes, and local food and brews in an open-air. Fell’s Point Fun Festival   Fell’s Point Fun Festival  – Oct 10–12, 2025. Baltimore’s longest-running neighborhood festival (est. 1967) takes over the historic Fell’s Point waterfront for its 59th year . This free street festival spans six blocks with multiple stages of live rock, blues and folk music , an outdoor “food & drink” court featuring Chesapeake favorites, dozens of arts/crafts vendors, and family amusements. Born from a successful effort to save Fell’s Point from a highway project, the Fun Festival today is a massive celebration of the area’s preservation and quirky maritime heritage . Baltimore Running Festival (Marathon)   Baltimore Running Festival (Marathon)  – Oct 18, 2025. A major annual running event featuring a marathon, half-marathon, 10K and 5K that start and finish at the Inner Harbor. 2025 marks the 25th anniversary of the Baltimore Marathon , and over 10,000 runners are expected to pound out citywide courses past Baltimore’s landmarks (Camden Yards, Federal Hill, etc.). Crowds of spectators line the streets to cheer, and the festival atmosphere at the finish line includes bands, beer gardens and celebratory crab medals – all reasons Runner’s World  has praised Baltimore as a top urban marathon. (The marathon’s longevity and 370,000+ total registrants  over the years attest to its popularity .) Great Halloween Lantern Parade (Patterson Park) Great Halloween Lantern Parade (Patterson Park)  – Oct 25, 2025. A uniquely Baltimore spooky-season tradition: at dusk, hundreds of handmade lanterns and floats illuminate Patterson Park in a magical nighttime parade . Organized by the Creative Alliance for 26 years, the event includes an afternoon family festival with costumes, pumpkin carving and Día de los Muertos performances, followed by the lantern parade after dark. Giant glowing puppets, community drum teams, and creatively lit “float” creations wind through the park, ending with fireworks. It’s an enchanting community arts spectacle that draws thousands of neighbors each year. Baltimore Ravens Home Games Baltimore Ravens Home Games  – Every fall Sunday at M&T Bank Stadium becomes an event in itself as the Ravens play before 70,000 passionate fans. NFL games in Baltimore are known for their energetic tailgates and deafening crowd (the stadium seats ~71,000 ) . In fall 2025, key matchups (e.g. division rivals like Pittsburgh) will fill downtown with purple jerseys. Even non-fans feel the civic pride – wins are celebrated citywide, and the “Ravens Flock”  make these games some of the loudest, most spirited gatherings in Maryland each autumn. 2025 Baltimore Ravens Home Games (Baltimore, MD): September 14: vs. Kansas City Chiefs September 28: vs. Pittsburgh Steelers October 12: vs. Cincinnati Bengals October 26: vs. Cleveland Browns November 9: vs. Miami Dolphins November 23: vs. New England Patriots December 14: vs. Los Angeles Chargers December 28: vs. Jacksonville Jaguars Maryland Terrapins Football (College Park) Maryland Terrapins Football (College Park)  – The University of Maryland’s football season runs through fall, with Big Ten conference games bringing tens of thousands out to College Park’s Capital One Field. In 2025 the Terps’ home schedule includes marquee opponents like Michigan and Penn State, promising big crowds and lively student section antics. UMD’s Homecoming game (usually October) is a festive affair with parades and alumni events. While not in the immediate Bay area, Terps football is a fall staple for many Maryland sports fans, often mentioned alongside the region’s pro games as a must-see event. 2025 Maryland Terrapins Home Games (College Park, MD): August 30: vs. Towson September 13: vs. West Virginia September 20: vs. Michigan October 4: vs. Indiana October 18: vs. Penn State (Homecoming) November 1: vs. Northwestern November 15: vs. Michigan State Baltimore Comic-Con Baltimore Comic-Con  – Oct 17–19, 2025 at the Baltimore Convention Center . A nationally recognized comic book and pop culture convention now in its 25th year, Comic-Con draws creators, vendors, and fans from far and wide. The 2025 edition will feature celebrity guest artists and writers, cosplay contests, discussion panels, and an exhibitor hall full of comics, collectibles and art. Baltimore Comic-Con has been lauded for its friendly vibe and top-notch guest lineups, making it a hit among both hardcore comic enthusiasts and casual fans. Baltimore Book Festival   Defenders’ Day at Fort McHenry  – Sept 12–14, 2025. Baltimore’s oldest historic commemoration marks the anniversary of the 1814 defense of the city and the writing of “The Star-Spangled Banner.”  At Fort McHenry National Monument, the weekend includes War of 1812 reenactors, cannon firing demonstrations, flag ceremonies, and educational programs for all ages . A parade through the Locust Point neighborhood and evening fireworks over the fort cap off the celebration . For history buffs, this is a moving tribute to Baltimore’s heritage – and for everyone else, it’s a chance to enjoy a patriotic display on the very grounds that inspired the national anthem. Closing: Celebrating Fall the Chesapeake Way Autumn in the Chesapeake Bay region is more than just a change of season — it’s a celebration of everything that makes this place special. From schooner races on crisp October mornings to lantern-lit parades in Baltimore, from the roar of Ravens and Navy football crowds to the timeless traditions of the Renaissance Festival and Blessing of the Fleet, fall here is filled with experiences that connect people to history, culture, and community. Whether you’re a local rediscovering old favorites or a newcomer soaking it in for the first time, the Chesapeake invites you to make this season unforgettable. Pack your calendar, bring your sense of adventure, and savor the traditions that make Maryland’s fall one of the most vibrant times of the year.

As the leaves turn gold and the air grows crisp, the Chesapeake Bay region celebrates fall the best way it knows how — through food and drink. Autumn here means oyster roasts by the water, cozy tavern dinners, seasonal farm-to-table menus, and harvest festivals at vineyards and breweries. Whether you’re a seafood lover, a wine enthusiast, or someone simply looking for a hearty meal in a warm atmosphere, the Bay’s dining scene shines brightest in the fall. Oyster Roasts & Seafood Festivals Nothing says fall in Maryland like oysters. As the season opens in October, towns across the Bay celebrate with festivals that bring locals and visitors together. U.S. Oyster Festival – Leonardtown U.S. Oyster Festival – Leonardtown (St. Mary’s County):  The longest-running oyster celebration in the country, home to the National Oyster Shucking Championship and Oyster Cook-Off. Visitors rave about the “family atmosphere, great food, and unbeatable oyster variety.” Chesapeake Bay Maritime Museum OysterFest – St. Michaels Chesapeake Bay Maritime Museum OysterFest – St. Michaels:  A vibrant waterfront festival featuring oyster tastings, stew competitions, and live music. Highly rated for its “blend of heritage, food, and fun.” Eastport Oyster Festival – Annapolis Eastport Oyster Festival – Annapolis:  A lively neighborhood celebration combining oysters, craft beer, and music — praised for its “local, authentic Chesapeake vibe.” Farm-to-Table Dining & Seasonal Menus Fall is harvest season, and restaurants across the region spotlight local produce, meats, and seafood in creative seasonal dishes. Blackwall Hitch (Annapolis) Blackwall Hitch (Annapolis):  Known for Chesapeake staples with a seasonal twist. Fall menus feature pumpkin bisque, roasted root vegetables, and fresh rockfish. The Inn at Perry Cabin (St. Michaels) The Inn at Perry Cabin (St. Michaels):  A luxury Eastern Shore dining experience where chefs craft menus around seasonal harvests and Bay-to-table seafood. Guests describe it as “the definition of autumn elegance.” Woodberry Kitchen (Baltimore) Woodberry Kitchen (Baltimore):  A James Beard Award–winning restaurant renowned for its commitment to local farms and seasonal dishes. Fall highlights include hearth-roasted squash and apple desserts. Wineries, Breweries & Harvest Festivals With grape harvests and Oktoberfest celebrations in full swing, fall is one of the best times to sip your way through the region. Linganore Winecellars (Frederick County) Linganore Winecellars (Frederick County):  Hosts a popular Autumn Reggae Wine Festival and weekend tastings. Visitors love the “relaxed vibe, live music, and stunning vineyard views.” Running Hare Vineyard (Calvert County) Running Hare Vineyard (Calvert County):  Known for its Tuscan-inspired setting and seasonal wine dinners, perfect for a fall evening out. Heavy Seas Beer (Baltimore) Heavy Seas Beer (Baltimore):  A staple brewery with an acclaimed Oktoberfest brew and fall taproom events. Consistently praised for atmosphere and community feel. Cozy Taverns & Waterfront Dining Spots As evenings grow cooler, nothing beats gathering in a cozy tavern or by the water for comfort food and cocktails. Carrol’s Creek Café (Annapolis) Carrol’s Creek Café (Annapolis):  A local institution with stunning harbor views, famed for crab bisque and seasonal seafood specials. Blackwall Hitch (Annapolis) The Boatyard Bar & Grill (Eastport/Annapolis):  Beloved for its casual vibe, great oysters, and “community feel” — especially in the fall. The Brewer’s Art (Baltimore) The Brewer’s Art (Baltimore):  A Mount Vernon tavern known for house-brewed beers and hearty fall fare, set in a historic mansion with glowing wood interiors. Wrap-Up Fall in the Chesapeake isn’t just about beautiful foliage — it’s about flavors that connect land, water, and community. From oyster festivals to vineyard harvests, farm-to-table kitchens to cozy waterfront taverns, the region offers countless ways to savor the season. So whether you’re a local foodie or a visitor craving authentic Chesapeake flavor, autumn is the perfect time to taste your way through Maryland’s most celebrated traditions.

Autumn on the Chesapeake Bay is nothing short of magical. As summer’s humidity gives way to crisp breezes and golden sunlight, both newcomers and lifelong locals find new reasons to love Maryland’s tidewater region. Weekends fill up with sunset sails on the Bay, hikes under vibrant foliage, slurping oysters at festivals, hayrides to pumpkin patches,  and celebrating the area’s rich heritage at fall fairs. The following guide highlights the most popular and enriching fall activities across Greater Annapolis, the Eastern Shore, Southern Maryland, and Greater Baltimore – all with a warm, inviting Chesapeake twist. Seasonal Sailing and Boating Experiences Fall brings steady winds and clear skies, making it one of the best times to get out on the water. In fact, Annapolis – known as America’s Sailing Capital  – buzzes each October with back-to-back boat shows that turn the harbor into a floating festival . Whether you’re an experienced mariner or a curious first-timer, there are plenty of ways to enjoy the Bay’s boating scene this season: National Boat Shows in October Schooner Woodwind Annapolis – Schooner Woodwind  & Boat Shows:   Catch a ride on the 74-foot Schooner Woodwind  for a classic sailing cruise out of Annapolis Harbor. Passengers consistently praise it as “a wonderful sailing experience… a definite must-do while visiting Annapolis,”  noting that “the crew, boat and tour were all exceptional” . You can help raise the sails or simply relax with a local craft beer as you glide by the U.S. Naval Academy and historic downtown. Early October also brings the U.S. Powerboat Show and U.S. Sailboat Show to City Dock (e.g. Oct 3–6 and Oct 10–14 in 2024), drawing boat lovers from near and far to climb aboard hundreds of vessels and browse the latest gear . The atmosphere is eclectic and exciting – truly “waves of excitement”  in the heart of Annapolis . Skipjack Rebecca T. Ruark Tilghman Island – Skipjack Rebecca T. Ruark :   For a more historic adventure, head to Tilghman Island on the Eastern Shore and hop aboard the Rebecca T. Ruark , the Chesapeake’s oldest surviving skipjack (built in 1886 ). This National Historic Landmark oyster schooner offers intimate sails on the Choptank River and Bay, often timed for sunset. Guests describe the experience as nothing short of “magical”  – “the stable, peaceful ship moves along in silence with the wind,”  allowing you to fully absorb the beautiful vistas . Captain Wade Murphy Jr., a local legend, has helmed the Ruark  for decades and won more skipjack races than any captain alive , enriching each trip with stories of the Bay’s maritime heritage. Wm. B. Tennison Historic Cruise Solomons – Wm. B. Tennison Historic Cruise:   In Southern Maryland, the Calvert Marine Museum in Solomons offers seasonal public cruises aboard the Wm. B. Tennison , a quaint 1904-built “bugeye” boat converted to carry passengers. Relax on a one-hour sightseeing cruise  that circles the busy Solomons harbor and Patuxent River mouth  – you’ll pass fishing boats at the island’s docks, see the iconic Thomas Johnson Bridge from below, and catch views of handsome Patuxent Riverfront homes and the Navy base before turning back at historic Point Patience. With gentle breezes and fewer crowds, fall afternoons on the Tennison  are peaceful and scenic. (The museum runs cruises May through October, typically on weekends in fall ). It’s an easy, family-friendly way to savor life on the Bay while learning a bit of local history from the captain’s narration. Fall Foliage Hikes and Nature Trails A historic covered bridge in rural Maryland, framed by peak fall foliage.  Maryland’s woodlands and riversides come alive with color each autumn, offering spectacular settings for hikes and scenic drives. From the Eastern Shore’s golden marshes to the Piedmont’s crimson maples, leaf-peeping  is a favorite fall pastime for many Chesapeake region residents . For those looking to stretch their legs and immerse in the scenery, here are a few top trails and nature parks to experience the fall foliage: Eastern Neck National Wildlife Refuge Eastern Neck National Wildlife Refuge (Kent County):  Tucked near Rock Hall on the upper Eastern Shore, Eastern Neck NWR is often cited as “one of the best spots for leaf peeping”  in Maryland . This 2,200-acre island refuge at the mouth of the Chester River boasts a mosaic of hardwood forests, marshland, and quiet coves. Seven miles of trails  wind through groves of oak and pine that blaze with color in late October . As you hike, keep an eye out for wildlife; the fall migration brings thousands of waterfowl and songbirds to the refuge’s rich habitat . The sight of bald eagles soaring over the Chester, framed by brilliant foliage, is unforgettable. Whether you choose the short Boardwalk Trail to an overlook or the longer Boxes Point Trail, you’ll enjoy tranquil Bay views and vibrant nature on this secluded peninsula. Patapsco Valley State Park Patapsco Valley State Park – Daniels Area (Baltimore/Howard County):  Just west of Baltimore, Patapsco Valley State Park offers some of Central Maryland’s prettiest fall foliage in a convenient location. A favorite spot is near Daniels Dam  on the north branch of the Patapsco River, where trails meander along old stone ruins and river rapids. “Ellicott City down by Daniels Dam is beautiful”  for an autumn walk, one local leaf-peeper noted . Hiking the Daniels Access trail , you’ll be treated to golden-yellow sycamores and tulip poplars arching over the river, with reflections of red and orange leaves dancing on the water. After a brisk hike, consider a scenic drive down winding Falls Road (MD-25)  north of Baltimore – this charming country road was recently named the second-best drive for fall foliage in the U.S . It follows rolling farmland and woodlands that erupt in color each October, giving you a perfect casual tour of Maryland’s autumn countryside. Calvert Cliffs State Park Calvert Cliffs State Park (Calvert County):  Known for its dramatic fossil-filled cliffs on the Chesapeake, Calvert Cliffs SP in Southern Maryland is also a spectacular fall hiking destination . A 1.8-mile Red Trail  leads from the trailhead down through the forest to the Bay shoreline, crossing wooden bridges and skirting serene marsh ponds along the way. “This is where all of the beautiful colorful fall foliage resides,”  one guide notes – the creekside path is shaded by beech and poplar trees that glow orange and gold in late October . The walk takes about 45 minutes each way and is relatively flat, suitable for most ages (just wear good shoes, as the path can be muddy with fallen leaves ). At trail’s end, you’ll emerge onto a sandy beach with stunning views of the 30-foot clay cliffs , which themselves take on ruddy hues in autumn light. Many hikers pack a picnic to enjoy on the beach while searching for ancient shark teeth among the pebbles – a quintessential Calvert Cliffs activity – before trekking back through the peaceful woods. Fewer crowds in fall make this popular park even more enjoyable. Oyster Festivals and Fall Food Events As water temperatures cool, oyster season swings into high gear – and around the Chesapeake, that’s cause for celebration! Fall is prime time for oysters, crabs, and other Bay bounty , and you’ll find food festivals every weekend where locals and visitors mingle over delicious seafood. These events aren’t just about eating; they often feature live music, cooking contests, and small-town charm. Below are a few must-visit fall foodie events (with oysters  taking the spotlight, of course): U.S. Oyster Festival U.S. Oyster Festival – Leonardtown, St. Mary’s County:  Every October, Southern Maryland hosts the nationally renowned U.S. Oyster Festival, home of the National Oyster Shucking Championship . In 2024 it marked its 58th year on the third weekend of October (Oct 19–20, 2024) at the St. Mary’s County Fairgrounds . For an admission of around $15, attendees enjoy a full day of oyster shucking and cooking contests, live music, arts and crafts vendors, and of course oysters any way you want  – raw on the half-shell, fried, stewed, you name it . This festival has a friendly, county-fair vibe with big crowds of families and seafood lovers. The highlight is the shucking competition where master shuckers race to shuck two dozen oysters; winners here often go on to compete internationally. It’s a true slice of Chesapeake culture. (Fun fact: St. Mary’s County is also known for stuffed ham, and you might find that local specialty for sale alongside the oysters!). The 59th annual festival is slated for Oct 18–19, 2025 , showing that this tradition is still going strong. Chesapeake Bay Maritime Museum OysterFest Chesapeake Bay Maritime Museum OysterFest – St. Michaels, Talbot County:  On the Eastern Shore, the town of St. Michaels throws a beloved OysterFest  each fall at the Chesapeake Bay Maritime Museum (often in late October; e.g. Oct 26, 2024 ). Billed as “the Bay’s favorite fall festival,”  it invites visitors to sip, slurp and savor  Chesapeake oysters served every which way . The event is a feast for all senses: you can sample oysters from multiple local farms (raw or char-grilled), taste entries in the oyster stew competition , and cheer on contestants in an oyster- slurp-off   contest . Live bands play folk and bluegrass tunes, and the museum’s waterfront campus fills with tents offering regional food, craft beer, wine and spirits . It’s a family-friendly day too – kids love the interactive demonstrations (like watching Chesapeake watermen tong for oysters or seeing retriever dogs in action) and crafts activities. “Whether you prefer to sip, savor, or slurp,”  this festival truly has something for every oyster enthusiast . Be sure to arrive hungry and leave time to explore CBMM’s historic boats and exhibits while you’re there. Taste of Cambridge Taste of Cambridge – Cambridge, Dorchester County:  For a broader food festival with an Eastern Shore flair, the Taste of Cambridge  street festival is a fall favorite. This annual event (held in October, with Oct 12, 2024 as a recent date ) transforms downtown Cambridge into a lively open-air block party celebrating the town’s culinary scene and seafood heritage . Local restaurants compete in a crab cook-off – expect creative crab soup and crab cake recipes – and festival-goers get to taste and vote  for their favorites. There’s also plenty of diversity beyond crab: vendors dish out everything from oysters to barbeque, and you can wash it down with craft beer or fresh cider. Live bands perform on street corners, an area is set aside with games and face painting for kids, and local artisans set up booths with handmade wares . It’s a wonderful way to sample many Eastern Shore flavors in one place. The community spirit in Cambridge is warm and welcoming, with residents and visitors strolling the brick-lined streets, mingling and enjoying the autumn weather together. If you leave without trying a slice of the famous 10-layer Smith Island cake (Maryland’s state dessert) being sold by a church bake table – did you really experience a Maryland festival? Grab a piece to go! Pumpkin Patches and Family Farm Outings Nothing says wholesome fall fun like a trip to the farm for pumpkins, corn mazes, and cider donuts. Across the Chesapeake region, family-owned farms  throw open their gates each autumn with festivals that delight kids and adults alike. You can pick your own jack-o’-lantern, get lost in a corn maze, pet barnyard animals, and savor seasonal treats like apple cider and kettle corn. Here are a few top picks for a fall farm outing, each offering a unique slice of local life: Weber’s Cider Mill Farm – Parkville Weber’s Cider Mill Farm – Parkville, Baltimore County:  A beloved tradition for many Baltimore-area families, Weber’s is actually the oldest cider mill still operating in Maryland (over 75 years and counting). Every fall, their farm (just 20 minutes north of the city) bursts with classic fun: hayrides around the orchards, an expansive pumpkin patch  for picking your own, a mini hay-bale maze and “Boo Barn” for little ones, plus live music and even puppet shows on weekends . The country store and bakery at Weber’s are legendary – fresh-pressed apple cider, warm cider doughnuts, and homemade pies  draw lines of hungry visitors . (Don’t skip the apple cider slushies; as one student visitor put it, “the stresses of life melted away”  with each sip !) With friendly farm animals to visit and plenty of Instagram-worthy photo ops (sunflower fields and “pumpkin mountain,” anyone?), Weber’s manages to capture “both the energy and atmosphere of [the] comforting season” . It’s a perfect day-trip for all ages – just be sure to go early in the day or on a weekday if you want to avoid the biggest crowds, as this place is popular. Councell Farms – Cordova Councell Farms – Cordova, Eastern Shore:  Situated along Route 50 not far from Easton, Councell Farms is a destination for fall fun on the Eastern Shore. This family-run farm is famous for its “Field of Fun”  play area – a giant playground of farm attractions including a corn maze, hayrides, a jumping pillow, giant slides and more (all for a modest admission fee). The pumpkin patch here is extensive, offering a huge selection of all sorts of pumpkins  in different shapes and colors . After picking your pumpkins (or decorative gourds and mums), reward yourself with a treat from their farm stand – they scoop homemade ice cream  that many rave about (the sweet corn flavor is a surprise hit!). Weekends bring additional fun like food trucks, local craft vendors, and sometimes live music. Councell is also dog-friendly  (on leash), so you’ll see plenty of pups in autumn bandanas enjoying the scene . It’s a great pit stop if you’re traveling down to the beach in fall, or a destination in itself for a relaxed afternoon of kid-friendly activities amidst the pastoral beauty of Talbot County. Bowles Farms Corn Maze & Pumpkin Farm Bowles Farms Corn Maze & Pumpkin Farm – Clements, Southern Maryland:  For more than 25 years, Bowles Farm has been “a key agritourism destination”  in Southern Maryland known for hosting one of Maryland’s largest and most elaborate corn mazes. Each autumn they design a new giant maze theme – the 2025 maze featured a 25th anniversary cake  design cut into 8 acres of corn! Navigating the maze can easily take an hour or more, but along the paths you’ll find bridges and interactive quiz stations that add to the fun . (One visitor noted it was “the best $10 I’ve spent in a long time!”  for such an experience .) Beyond the maze, Bowles offers a full day of activities: a pumpkin patch  stocked with many varieties, wagon rides around the farm, a petting zoo with goats and sheep, a mini straw maze for toddlers, and even occasional events like tractor pulls . Families praise the friendly, down-home atmosphere – “so much to do for the kids,”  as one review noted, and yet also enjoyable for the parents . Don’t miss grabbing some snacks from the barn before you leave; Bowles Farm is locally famed for its baked goods  (their blueberry cobbler and pumpkin cupcakes are “astonishingly good,”  according to one Yelp review ). On busy October weekends, going early is wise (the farm advises visiting in the morning to avoid peak crowds ). With its mix of nostalgia and honest farm fun, Bowles Farm makes visitors “feel like part of the farm family”  and keeps them coming back fall after fall . Historic and Cultural Fall Festivals Autumn’s cooler days also set the stage for festivals that celebrate the Chesapeake region’s rich history and culture. Many communities host events that honor local traditions – whether it’s the legacy of early colonists and watermen, or simply the quirky customs that give a town its identity. These fall festivals offer more than entertainment; they’re a chance to connect with the Chesapeake’s heritage and people. Here are a few noteworthy cultural events to check out: Maryland Renaissance Festival Maryland Renaissance Festival – Crownsville (Anne Arundel County):   For nine weekends each late summer and fall, a patch of woods near Annapolis transforms into Revel Grove , a fictional 16th-century English village bustling with knights, minstrels, and merriment . The Maryland Renaissance Festival is one of the country’s largest renaissance fairs, drawing over 300,000 visitors a season . Open from late August through October (Saturdays and Sundays plus Labor Day), it’s an annual autumn tradition  for many families . Expect to find 10 stages of continuous entertainment  – from jousting tournaments with armored knights charging in a 3,000-seat arena, to comedy skits, musicians, and Shakespeare plays . More than 140 artisans set up shop in tudor-style buildings, selling handmade crafts like pottery, jewelry, and leatherwork . Of course, there’s food aplenty: giant turkey legs, meat pies, ales and mead at the taverns, and other Renaissance-era eats. Come in costume (many do), or just come as you are and enjoy the incredible people-watching. As a tourism site describes it, it’s “nine weekends of thrills, feasting, handmade crafts, entertainment, and merriment”  in the forest of Crownsville . The festival has been running since 1977 and has a devoted following – you’ll often see the same patrons returning multiple weekends to experience different themed days and shows. If you’re looking for a full day of escapism and fun that appeals to all ages, the Ren Fest is a must-visit. Pro tip: go in late September or October when the weather is cooler and the wooded village is decorated with fall flowers and pumpkins; the ambiance is unbeatable. Easton Waterfowl Festival Easton Waterfowl Festival – Easton (Talbot County):  Every November, as migrating ducks and geese arrive by the thousands on the Chesapeake, the town of Easton hosts the Waterfowl Festival – a unique heritage event celebrating wildlife, art, and Eastern Shore culture . Over three days (usually the second weekend of November, like Nov 8–10, 2024 ), downtown Easton becomes a sprawling venue for decoy carvers, painters, sculptors, and photographers  to showcase their work centered on waterfowl and nature. It’s essentially an art festival meets country fair: you can admire (or purchase) world-class duck decoys and watercolor landscapes in one hall, then step outside to hear live folk music and grab crab soup from a street stand. Events are spread across multiple sites – galleries, tents, and even Easton High School – with shuttle buses connecting them. Kids love the retriever dog demonstrations  and birds of prey exhibit, while adults often enjoy the calling contests or World Championship Duck Carving  competition. Don’t miss the food court featuring Eastern Shore specialties (yes, there are oysters and crab cakes, too!). The festival, now in its 50+ year, is run by volunteers and proceeds go toward wildlife conservation. It’s a community labor of love that has a charming throwback feel. As one description sums up, the Waterfowl Festival is “a three-day event celebrating Maryland’s Eastern Shore with wildlife art, antique decoys, retriever demos, seafood, live music, and kids’ activities” Even if you’re not a hunter or art collector, you’ll find something to enjoy – perhaps it’s the small-town hospitality and heritage pride that leave the biggest impression. Blessing of the Fleet Blessing of the Fleet – Southern Maryland (St. Clement’s Island/Leonardtown):  This century-old Southern Maryland tradition is a beautiful blend of history, faith, and community festivity. The “Blessing of the Fleet” originally began as a religious ceremony to bless the boats of local watermen  at the end of the work season , asking for safety and prosperity in the coming year. Today it has evolved into a family-friendly festival celebrating St. Mary’s County’s heritage  – but it still features an actual boat blessing ritual as its centerpiece. Typically held the first weekend of October, the event is hosted by the 7th District Optimist Club and for many years took place on the grounds of St. Clement’s Island Museum (site of Maryland’s first colonial landing in 1634). In 2024 and 2025, due to site renovations, it moved to Leonardtown Wharf Park – but the spirit remains the same . The day includes live music, local seafood and BBQ vendors, craft booths, a kids’ petting zoo and pony rides . Come late afternoon, attention turns to the water as a procession of decorated boats motors past to receive a ceremonial blessing from clergy, honoring the region’s watermen and sailors. There’s a strong sense of community pride on display – the event “celebrates local watermen and the heritage of St. Mary’s County”  with everything from traditional gospel singers to exhibits on maritime history . After sunset, everyone settles in for an outdoor concert and often a fireworks show  over the Potomac River, which lights up the autumn sky and the gleaming boats at anchor. It’s a heartfelt reminder of Southern Maryland’s roots. As one local put it: Blessing of the Fleet  isn’t just about the boats, it’s about blessing the community and its way of life. From sailing on brisk October afternoons to wandering through corn mazes and historic towns, fall in the Chesapeake Bay region offers a wealth of experiences that are both fun and deeply fulfilling. It’s a time when the Bay’s natural beauty and cultural traditions truly shine. So grab a sweater, pack your sense of adventure, and get out there to discover these fall favorites for yourself – whether you’re shucking oysters by the water  or hiking under fiery maples , the Chesapeake autumn will warmly welcome you. Enjoy!

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