13 Maryland Fall Festivals Where The Food Alone Makes The Trip Worth It
Maryland comes alive each autumn with festivals that celebrate the harvest season in delicious ways.
From the Chesapeake Bay’s famous oysters to fresh apple cider pressed right before your eyes, these gatherings offer some of the best regional food you’ll find anywhere.
Whether you’re craving seafood straight from the water or homemade treats from local farms, these festivals prove that fall in Maryland tastes as good as it looks.
1. Maryland Renaissance Festival (Crownsville)
Step back in time at this legendary festival where giant turkey legs reign supreme and the feasting never stops. Vendors serve up hearty medieval fare like steak on a stake, roasted corn, and meat pies that would make King Henry jealous.
The food court stretches across multiple areas, each offering different specialties from sweet funnel cakes to savory sausages. You can munch on fresh pretzels while watching jousting tournaments or sip hot cider between shows.
Running weekends from late August through October, this festival transforms a wooded area into a bustling 16th century village complete with entertainment and endless eating opportunities.
2. U.S. Oyster Festival (Leonardtown)
Raw, steamed, fried, or in a stew, oysters take center stage at this Southern Maryland celebration that draws seafood lovers from across the region. Professional shuckers compete in speed contests while you sample the Chesapeake’s finest bivalves prepared dozens of different ways.
Beyond oysters, the festival serves crab cakes, clam chowder, and fish sandwiches that showcase local watermen’s daily catches. Live music fills the air while you explore craft vendors between food stops.
Held in mid-October, this event perfectly captures Maryland’s maritime heritage on a plate.
3. OysterFest At Chesapeake Bay Maritime Museum (St. Michaels)
Picture yourself eating freshly shucked oysters on the water’s edge while learning about the watermen who harvest them. This festival combines education with incredible eating, offering tastings from multiple oyster farms around the bay.
Food trucks and local restaurants set up booths serving everything from oyster sliders to seafood mac and cheese. The museum setting adds charm you won’t find at typical fairgrounds.
Usually scheduled for early November, this event lets you explore maritime history between bites of perfectly prepared shellfish that taste like the Chesapeake itself.
4. Autumn Glory Festival (Oakland)
Western Maryland’s mountains provide the backdrop for this five day celebration where Appalachian food traditions shine brighter than the fall foliage. Buckwheat pancake breakfasts kick off mornings, followed by barbecue competitions that fill the air with smoky goodness.
Local vendors dish out homemade pies, apple butter, and regional specialties you won’t find closer to the coast. I once tried their famous bean soup at this festival and went back for seconds before even finishing my first bowl.
Taking place in early October, this event offers mountain hospitality with flavors that warm you from the inside out.
5. Rock Hall FallFest (Rock Hall)
This charming fishing village throws a party where steamed crabs meet autumn vegetables in perfect harmony. Crab soup bubbles in huge pots while vendors grill rockfish caught that morning in the bay.
Sweet potato fries, corn fritters, and pumpkin desserts add seasonal flair to traditional seafood offerings. The waterfront location means you’re eating with boats bobbing in the background and seagulls hoping for scraps.
Scheduled for late September, FallFest captures the transition from summer’s seafood bounty to autumn’s harvest in one delicious weekend that celebrates both.
6. Maryland Seafood Festival (Annapolis)
Sandy Point State Park transforms into seafood heaven each September with more varieties of fish, crabs, and oysters than you can count. Dozens of restaurants and vendors compete for your attention with their signature dishes and secret recipes.
Crab cakes the size of hockey pucks, creamy she-crab soup, and blackened rockfish tacos represent just a fraction of what’s available. You could spend the entire day eating and still not try everything.
This festival proves why Maryland earned its reputation as a seafood paradise, serving up bay treasures with a side of live entertainment.
7. Ocean City Sunfest (Ocean City)
When summer crowds disappear, Ocean City hosts this relaxed festival where boardwalk treats meet serious seafood in a celebration of coastal cuisine. Fresh squeezed lemonade washes down everything from soft shell crab sandwiches to Thrasher’s famous fries that need no ketchup.
Local restaurants showcase their best dishes while food trucks add variety with fusion options and creative twists on classics. The ocean breeze makes outdoor eating even better than usual.
Happening in late September, Sunfest offers beach town vibes without the summer heat, making it perfect for leisurely eating and strolling.
8. Darlington Apple Festival (Darlington)
Apples steal the show at this northern Maryland tradition where orchards share their harvest in every form imaginable. Fresh pressed cider flows freely while vendors sell apple dumplings, fritters, and pies still warm from the oven.
Caramel apples get dipped right before your eyes, and apple butter simmers in copper kettles using recipes passed down through generations. The whole town smells like cinnamon and autumn.
Held the first Saturday after Labor Day, this festival has celebrated apple season since 1976 with country charm and treats that taste like grandma’s kitchen.
9. Summers Farm Fall Festival (Middletown)
Farm fresh flavors dominate this Frederick County celebration where everything tastes better because it was probably growing nearby last week. Kettle corn pops in huge batches while food trucks serve up creative comfort food using local ingredients.
Pumpkin flavored everything appears on menus, from donuts to soups to desserts that showcase the season’s star ingredient. Kids can munch on treats between corn maze adventures and hayrides.
Running weekends September through November, this working farm festival combines agricultural fun with serious eating opportunities that highlight Maryland’s farming heritage beautifully.
10. Weber’s Cider Mill Farm Fall Harvest Days (Parkville)
Watch apples transform into golden cider at this working mill that’s been pressing fruit since 1930s using equipment that still works like a charm. Hot cider donuts emerge from the fryer throughout the day, their sugar coating glistening under autumn sunshine.
Fresh pressed cider tastes nothing like store bought versions, with complex flavors that change based on which apples went into the press. My kids once ate four donuts each here before I could stop them, and honestly, I understood completely.
Open select fall weekends, this spot offers authentic farm experiences with treats worth the trip alone.
11. Montpelier Farms Fall Festival (Upper Marlboro)
Southern Maryland agriculture shines at this Prince George’s County farm where seasonal treats satisfy hungry festival goers exploring acres of autumn activities. Barbecue pits smoke all day while vendors serve everything from funnel cakes to corn on the cob slathered in butter.
Local food trucks add variety with tacos, sliders, and creative dishes that complement traditional fair food perfectly. Pumpkin patches and farm animals provide entertainment between eating sessions.
Weekends throughout October bring families back repeatedly because the food stays fresh and the menu changes enough to keep things interesting every visit.
12. Milburn Orchards Fall Festival Weekends (Elkton)
Cecil County’s premier orchard opens its fields for fall fun fueled by some of the best farm market food in the state. Apple cider slushies provide cold refreshment while hot apple crisps warm you up when temperatures drop.
Their farm kitchen bakes pies, cookies, and pastries using fruit picked that morning from trees you can see from the picnic tables. Grilled items and seasonal soups round out a menu designed for outdoor eating.
Running weekends September through October, this festival lets you pick your own apples then immediately eat treats made from identical fruit.
13. Catoctin Colorfest (Thurmont)
Mountain town streets close down for this massive two day event where over 350 vendors include some of the best festival food you’ll encounter anywhere. Funnel cakes compete with gourmet options while traditional fair treats share space with ethnic cuisines from around the world.
Barbecue, seafood, Italian sausages, and Greek specialties all appear within blocks of each other. The mountain setting and fall colors make outdoor eating feel special.
Held the second weekend in October, Colorfest draws huge crowds who come as much for the food variety as the crafts and scenery surrounding this Frederick County gem.