October brings plenty of ways to get out and enjoy the season around Annapolis! From waterfront festivals and local food to giant pumpkins and fall traditions, there’s something for everyone to enjoy throughout the month.
Maryland Corn Maze
Weekends in October
Get lost in the fun at the Maryland Corn Maze! 🌽 Navigate your way through the twists and turns, enjoy classic fall activities, and make a day of it with family and friends.
Maritime Heritage Festival
October 3
Take a trip back in time at the Galesville Maritime Heritage Festival, where you can experience the area’s rich connection to the Chesapeake Bay. ⚓ Enjoy maritime activities, local history, food, and fun for the whole family.
Great Annapolis Pumpkins
Beginning October 5
Keep an eye out for giant pumpkins popping up around Annapolis throughout October! 🎃 These massive pumpkins will be on display across the city before they’re carved at the end of the month, making for a fun fall tradition to watch unfold.
DragonFest
October 17
Step into a world of dragons, fantasy, and family fun at DragonFest! 🐉 Enjoy a day filled with themed activities, entertainment, and plenty of opportunities to embrace your inner adventurer.
Oyster Festival
October 17
Celebrate Maryland’s favorite shellfish at the Oyster Festival! 🦪 Enjoy fresh oysters, local food, live music, and a fun day by the water while learning more about the Chesapeake’s maritime heritage.
Feast on the Farm
October 24
Enjoy an evening on the farm at Feast on the Farm, a celebration of conservation, local food, and the Chesapeake landscape. 🌾 It’s a great way to enjoy a delicious meal while supporting efforts to protect the places that make Maryland special.
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