Local Events Guide
Spring & Summer in Annapolis
April
Bay Bridge Boat Show
April 17 – 19
One of the largest in-water powerboat shows in the Mid-Atlantic, featuring motorboats, gear, and the latest in marine technology.
Powerboat Details →The Annapolis Cup: St. John’s vs. USNA
April 18
The legendary croquet match and 1920s-style garden party between the "Johnnies" and the "Midshipmen." A true community highlight.
Ticket Release Info →Annapolis Spring Sailboat Show
April 24 – 26
Tour world-class sailboats, attend workshops, and enjoy the maritime culture at City Dock as the sailing season officially begins.
Sailboat Show Tickets →May
71st Annual May Day Baskets
May 1
A signature tradition where residents and businesses adorn their doors with fresh-cut flower baskets to welcome spring.
View Walking Route →USNA Commissioning Week
May 16 – 22
Highlighting the Naval Academy’s graduating class. Includes the Blue Angels flight demonstrations (May 19-20) and graduation.
Full Schedule →Dinner Under the Stars Kick-off
Starts May 20
Every Wednesday evening, West Street closes for alfresco dining, live music, and dancing under the café lights.
Restaurant List →Annapolis Irish Festival
May 29 – 30
Two days of Celtic music, bagpipes, and family activities at the Anne Arundel County Fairgrounds.
Ticket Info →June
Let’s Go Music Festival
June 5 – 6
Summer’s major music event featuring a national lineup of artists at the Anne Arundel County Fairgrounds.
Artist Lineup →First Sunday Arts Festival
June 7
Explore over 100 local artisans along West Street. Live music, street performers, and local food vendors.
Vendor Map →Annapolis Juneteenth Celebration
June 19 – 20
Commemorate the holiday with a community parade through downtown followed by a festival featuring heritage displays and live music.
Parade Route →