22 Miles to Break Boundaries Festival & Run
Don’t miss the 22 Miles to Break Boundaries Festival and Run! Bring the whole family to enjoy face painting, yard games, kids activities, food trucks serving up local favorites, vendor …
Art on the Avenue
Don’t miss Art on the Avenue! Artists’ paintings of Annapolis’ Historic District will be on display along Maryland Avenue during this fantastic street festival from 6:00 pm – 8:00 pm. …
Katherine’s Light Foundation Music Festival & Charity Event
Join Bach to Rock and other great performers on the acoustic stage as we raise funds to support Katherine’s Light Foundation at Severna Park Taphouse.
Father’s Day on the Bay to St. Michaels
Enjoy Father’s Day with a cruise across the Chesapeake Bay to St. Michaels on the Eastern Shore. This quaint historic village offers fresh seafood, boutique shopping, and historic sites all …
Free – Latin American Children’s Day Festival (el dia de los ninos)
Everyone is welcome. Enjoy free food and entertainment at this family-friendly event.
50th Kent Island Day 2025
It’s the 50th anniversary of the Kent Island Heritage Society! Each year, on the third Saturday of May, Kent Island Day commemorates the founding of Kent Island in 1631 with …
Video Game Music Concert
Video Game Music Concert Featuring Ravita Jazz & Saxophonist Herb Scott May 4 from 4 – 6 PM Eastport United Methodist Church 926 Bay Ridge Avenue Annapolis, MD 21401 410-263-5490 …
Illuminate Annapolis
The Illuminate Annapolis Mind-Body-Spirit-Arts Festival will be held at Anne Arundel Community College. Exhibitors may include aura photography, energy work, crystals, essential oils, vetted intuitive readers including tarot, psychic mediums, …
Neo Soul Wine Festival
Welcome to the DMV Neo Soul Wine Festival. A place where good times and great wines collide! Get ready to experience a day filled with soulful sips, fantastic flavors, and nothing but …
Crab Feast
The 80th annual Rotary Club of Annapolis Crab Feast will be held on Friday, August 1, 2025 from 5:00 pm to 8:00 pm at the Navy-Marine Corps Memorial Stadium in …