Celebrate Summer with SoulJourners
Get ready for a special event in the maritime heart of Annapolis. On Sunday, July 26, Annapolis Jazz & Roots will invite music loving residents and visitors to Eastport United …
Annapolis Pride Parade & Festival
Don’t miss the Annapolis Pride Parade & Festival on October 3, 2026! The parade will start in downtown Annapolis at 11:00 am, and the festival will take place at the …
Official Baygrass Kick-Off Party w/ Jammy Buffet
Join us on Friday, September 18 for the Official Baygrass Kick-Off Party! Enjoy an evening of live music, great food, and cold drinks at Maryland Hall in Annapolis, MD. Cumberland …
CRAB Cup
The CRAB Cup is a family-friendly sailing event hosted by the members and professional staff at Eastport Yacht Club. Founding sponsor Boatyard Bar and Grill serves a gourmet buffet to many hungry …
For the Love of the Library
Don’t miss For the Love of the Library! Let’s celebrate the library and raise support for all it makes possible! The experience includes an author event with Nikki Payne, an …
Cheer on the World Cup Around Annapolis
Once every four years, the greatest soccer teams on Earth come together for the World Cup. This year has been extra special for a couple of reasons. First, the tournament …
Pizza Party + Playtime
Grab a spot and join us for pizza and playtime on Friday, July 24 from 4:30 pm-6:00 pm! No need to feed the kiddos before you arrive! We will provide …
Annapolis Blues Watch Party
Don’t miss the Annapolis Blues vs Virginia Beach United watch party! It will take place at West End Grill on July 8, 2026. (DNML)
Oktoberfest
Raise a glass to this year’s Oktoberfest! We’re happy to partner once again with RAR Brewing and Chessie’s Wharf as our beer garden sponsors. Savor an ice-cold brew, feast on …
Maryland Renaissance Festival
The Maryland Renaissance Festival, a tradition for the entire family, begins its 50th season on August 29th and runs Saturdays and Sundays and Labor Day Monday through October 25th for nine …