Fall Adventures Around Chesapeake Bay: Sailing, Trails, Oysters & More

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!