Annapolis MD Community Events

Greenstreet Gardens Fall Festival

September 17th – October 30th
391 West Bay Front Road, Lothian, MD 20711
Join Greenstreet Gardens in for their fall festival happening six weekends in a row. Bring the little ones and enjoy their 5-acre corn maze, pumpkin bowling, haunted hay rides, and much much more! 

U.S. Sailboat Show

October 5th – 9th
City Dock, Annapolis
More than 50,000 boating enthusiasts from around the world will be attending the nation’s oldest and largest in-water sailboat show. This world wide recognized event is in it’s 48th year. Come out to America’s Sailing Capitol! 

Oyster Festival

October 16th from 12:30 pm – 5:00 pm
Captain Avery Museum, 1418 East West Shady Side Road, Shady Side
Attention seafood lovers! Come out and enjoy live music, unique crafts, face painting, and oysters! There will be fried oysters, oyster stew, and oyster sushi rolls (YUMMY!).