The Santa Maria Cup
The Santa Maria Cup is one of the premier women’s match racing regattas in the world. Hosted annually by Eastport Yacht Club in Annapolis, Maryland, the event brings together top …
22 Miles to Break Boundaries
22 Miles to Break Boundaries is a nationwide movement honoring our nation’s military heroes—and a call to action to fund life-saving brain health and suicide prevention programs. Join from anywhere …
Race and Rights Tour
Don’t miss this Race and Rights Tour! Join presenter Briayna Cuffie on this 50-minute guided tour of the Museum that highlights the powerful contributions of African American community leaders in …
Annapolis 10 Mile Run
The Annapolis 10 Mile Run is a 10-mile foot race organized by the Annapolis Striders, Inc., a 1000 member, all volunteer, non-profit 501(c)(3) organization. Established in 1978 in Annapolis, Maryland, …
Washington College Invitational College Crew Regatta
The Gunston School will proudly host the Washington College Invitational College Crew Regatta on Saturday, March 21, welcoming multiple collegiate rowing programs to compete on the Gunston waterfront. The event …
Run for the Trees: Happy Little 5K
Enjoy the awesome scenery of the Chesapeake Bay as you participate in the Sandy Point Happy Little 5K! Register here!
Anne Arundel County Police 5K Run
Please join us for a 5K run to benefit the Anne Arundel County Police Unity Tour Team. The Police Unity Tour helps raise awareness for officers who have fallen in …
Annapolis RUN for The Light House – HALF, 5k, Walk
17th Annual Annapolis RUN for The Light House provides scenic routes along the trails of Quiet Waters Park and through the beautiful Chesapeake Bay-front community of Hillsmere Shores. SOLD OUT …
Annapolis Striders’ Valentine’s 5K
Runners of all ages and abilities are invited to join us at the Annapolis Striders’ first formal race of 2026, the Valentine’s 5K, taking place on Saturday, February 14, 2026 …
2026 Winter Island 5K & 10K
Don’t miss the 2026 Winter Island 5K & 10K! It will take place on January 18, 2026 from 8:30 am to 11:00 am at Matapeake Park. Register here!