Fall 2025 Festivals & Events in the Chesapeake Bay Region (Maryland)

Shane Hall
Sep 9
9 min read

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 (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) – 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 – 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 – 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) – 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) – 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 – 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 – 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) – 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) – 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) – 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 – 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 (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) – 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) – 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) – 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 – 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 – 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) – 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) – 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 – 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) – 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 – 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.

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.

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