Calendar of Events

This is a calendar of events taking place on and around the Chesapeake Bay for the months of April, May, and June.  The calendar includes a wide variety of events including festivals, boat races, boat shows, fishing tournaments, exhibitions, seminars and workshops.

Return to the Calendar index page to select different months.

April – June 2025

April 11 -13, 2025 – Bay Bridge Boat Show – Annual powerboat show at Safe Harbor Narrows Point in Grasonville, MD.

April 25 – 27, 2025 – Annapolis Spring Sailboat Show – Big annual in-water boat show held at Annapolis City Dock. Annapolis, MD.

May 17, 2025 – Kent Island Day – A celebration of the heritage, life, and culture of Kent Island, sponsored and organized by the Kent Island Heritage Society. Takes place annually on the third Saturday in May.

May 17 & 18, 2025 – Cambridge Classic Powerboat Regatta – The oldest active powerboat race in the country.  Two days of racing on Hambrooks Bay off the Choptank River. Cambridge, MD.

May 23 – 25, 2025 – Chestertown Tea Party Festival – Annual festival centered around the reenactment of the 1774 tossing of tea cargo into the Chester River in protest of the British Parliament’s closing of the port of Boston. The festival includes Tea Toss Reenactment, Colonial Parade, street performances, colonial crafts, strolling musicians, local fare, and more. Chestertown, MD.

June 6 – 8, 2025- Norfolk Harborfest – Norfolk’s big annual waterfront festival with visiting tall ships, live music, food vendors, Navy exhibits and demonstrations, a large fireworks display, and more. Town Point Park. Norfolk, VA.