Annapolis Fall Festivals: Top Events and Activities Nearby

In Annapolis, Maryland, the fall season highlights the city’s waterfront charm with a lineup of lively festivals. The Maryland Seafood Festival at Sandy Point State Park on Sept. 8–9 celebrates the flavors of the Chesapeake Bay during its 51st annual crab soup cook-off. Attendees can sample local seafood, craft beers and wines, watch cooking demonstrations, and enjoy activities for children.

© Maryland Seafood Festival

The Anne Arundel County Fair returns for its 66th year at the Anne Arundel County Fairgrounds Sept. 12–16. The fair offers family-friendly entertainment including pig races, camel rides, car racing, wood carving demonstrations, and demonstrations that introduce visitors to traditional fairground skills like hog calling.

The Amps and Ales Craft Beer and Music Festival at the Arundel Mills Entertainment District on Sept. 15 features more than 40 craft beers from local breweries and live music. The event also showcases a wide selection of food trucks, offering choices such as wood-fired pizza, crab cakes, and other regional favorites.

The 16th Annual Oyster Festival at the Captain Avery Museum on Oct. 21 is a celebration of oysters in many forms—raw, fried, in stews, and in creative preparations like fried oyster roll sushi. The festival focuses on family-friendly entertainment alongside plentiful food options.

Maryland Renaissance Festival © VisitAnnapolis.org

Through Oct. 21, the Maryland Renaissance Festival transforms its grounds into a 16th-century English village on weekends. Visitors can enjoy performances by jugglers, musicians, comedians and magicians, browse 130 craft shops, dine on themed fare, and watch reenacted medieval combat in a 3,000-seat jousting arena.