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 2024

April 12, 2024 – Bay Bridge Boat Show – Annual powerboat show at Bay Bridge Marina in Stevensville, MD.

April 26 – 28, 2024 – Annapolis Spring Sailboat Show – Big annual in-water boat show held at Annapolis City Dock. Annapolis, MD.

May 18, 2024 – Tour de Chesapeake – Annual family-friendly cycling event with routes traveling the scenic (and flat!) terrain of Matthews County, Va.

May 18, 2024 – 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 18 & 19, 2024 – 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 24 – 26, 2024 – 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 tarty, raft race, street performances, colonial crafts, strolling musicians, local fare, and more. Chestertown, MD.

June 7 – 9, 2024- 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.

June 12 – 18, 2024 – Maryland Fleet Week and Flyover Baltimore. A week of festivals, visiting ships, and military flyovers. Held in multiple locations.