Oyster Festival
As always, our Oyster Festival—winner in the past of the Bay Weekly Best of the Bay award for Community Events—features good community company, fine regional music, an array of choice …
Fall Harvest Festival + War of 1812
Don’t miss this Fall Harvest Festival + War of 1812 event! Learn about African Americans during the War of 1812 and the contributions of African Americans at Hancock’s Resolution with …
Fall Fun Day
Don’t miss this Fall Fun Day at Kinder Farm Park! It will take place on October 11 from 10:00 am to 3:00 pm. There will be a pumpkin patch, hayrides, …
Maryland Sheep & Wool Festival
The Maryland Sheep & Wool Festival is one of the largest festivals of its kind celebrating all things sheep, from hoof to handwoven. The Maryland Sheep & Wool Festival will …
Odenton Day
On Saturday, October 4 from 9:00 am to 2:00 pm, the Odenton Heritage Society will open its doors for the town’s annual celebration of Odenton Day, a joint effort by …
Annapolis Pride Parade & Festival
Get your costume ready for some spooky fun! The Annapolis Pride Parade and Festival will be held on October 18. Parade starts at 10:00 am at Calvert and Bladen streets, …
Barktoberfest
Who let the dogs out, again?! Join us for the third Barktoberfest with steins and canines as we celebrate German-style beer, bavarian food, and pawesome four-legged friends. Get your tickets …
Annapolis Chocolate Binge Festival
The Inner West Street Association brings you the popular Annapolis Chocolate Binge Festival to downtown Annapolis for the holidays. Held on Sunday, December 7, 2025 from 11:00 am to 4:00 …
Homestead Gardens’ Fall Festival Weekends
Join us for Fall Festival Weekends at Homestead Gardens: Davidsonville! Give your family the same enchanting experiences you had as a child—seeing the barnyard animals, taking hayrides, picking out pumpkins, …
Know Before You Go: Annapolis Songwriters Festival
Annapolis is turning the volume up! The Annapolis Songwriters Festival, presented by Rams Head Presents in partnership with BMI, Visit Annapolis & Anne Arundel County, and the City of Annapolis, …