Chesapeake Bay Region Calendar of Events: April – June
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. This includes events for Maryland’s Eastern Shore, Eastern Shore of Virginia, Southern Maryland, and Virginia’s Northern Neck, Middle Peninsula, and Hampton Roads. 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.
April 26, 2025 – Oxford Day – This annual festival includes activities such a parade, flower sale, Blessing of the Animals, Dog Walk and Dog Show, Library Book Sale, Opening Day of the Oxford Museum, and free walk-on Ferry Rides on the Oxford Bellevue Ferry. Oxford, Maryland.
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.