Haunted Harbour Day
Don’t miss Haunted Harbour Day! Slip into your favorite costume and get ready for a day of Halloween magic! This free, family friendly Halloween event includes: Trick or treating Free …
The Haunted Hill of North Shore
The Haunted Hill of North Shore is letting us use their awesome trail once more to raise money for Jamz Boosters at Jamz Dance Studio! Stop in October 11, 12, …
Halloween Bash
Our annual Halloween Bash includes live music, food, drinks, and more! Proceeds go to support The Bernie House, a local Annapolis charity providing resources to survivors of domestic violence. Join …
Living History on Pinkney Street: 250th Anniversary of the Burning of the Peggy Stewart
In October of 1774, the people of Annapolis discovered that the brigantine, the Peggy Stewart, contained contraband tea that violated the colonists’ non-importation resolution. In response to public outrage, ship …
Family Fall Festival
Join Waugh Chapel Towne Centre on South Main Chapel Way for their annual Family Fall Festival on Saturday, October 19, 2024 from 12:00 pm to 2:00 pm!* Visit for balloon …
Trick or Treat Trail
Don’t miss the Trick or Treat Trail! It’s that spooky time of year again. Join the Friends of Downs Park for our annual Halloween Trail and Pumpkin Patch event. Available …
Dia De Los Muertos
Join us for folkloric artists, traditional Mexican food, attractions for children, raffles, community resources, dancing, and celebration on Dia De Los Muertos! This Dia De Los Muertos (Day of the …
Masquerade Ball
Enter the street with glam and glimmer as you dine during an evening of entertainment at Dinner Under the Stars‘ Masquerade Ball! Dance to the music of Naptown’s DJ Michael …
Party in the ‘Port—Boat Show Edition!
Join the excitement at Party in the ‘Port! Eastport Yacht Club’s premier boat show celebration is open to everyone! Enjoy electrifying live music from Dublin 5, soak in the vibrant …
Oyster Festival
As always, the 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 …