Homegrown & Handmade OctoberFest
Now more than ever, it feels important to come together as a community. With so much going on, we take joy in supporting our fellow local makers, farmers, and small …
Annapolis Pride Parade Is Back and Ready to Slay
Annapolis, get ready to strut your stuff! The Annapolis Pride Parade & Festival is back for its fifth year, set for October 18, 2025. Each year, families, friends, and allies …
ARToberfest
Celebrate creativity and community at ARToberfest on Saturday, October 4, 2025 from 11:00 am – 3:00 pm in the charming Stevensville Arts & Entertainment District. This free, all-ages event will feature live music, …
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 …