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 2023

April 22 – 23, 2023 – Eastern Shore Sea Glass and Costal Arts Festival – Held at the Chesapeake Bay Maritime Museum. This event features artisans from around the country with coastal and sea-glass related jewelry, home décor, art, items available for sale. Admission includes access to CBMM exhibits.

April 28 – 30, 2023 – Annapolis Spring Sailboat Show – Big annual in-water boat show held at Annapolis City Dock

May 3 – 7, 2023 – Annapolis Up-Rigging – Tall ships visit Annapolis and offer tours and sailing for guests. There is also a festival with vendors and live music.

May 19 – 26, 2023 – US Naval Academy Commissioning Week – Naval Academy graduation weeks is celebrated with special events and activities including a flight demonstration by the Blue Angels.

May 20, 2023 – St. Michaels Running Festival – This fest has the bragging rights as the flattest 13.1 in the Mid-Atlantic. Courses available include a half marathon, 10K Run and 5K Fun Run/Walk.

May 20 & 21, 2023 – Cambridge Classic Powerboat Regatta – The oldest active powerboat race in the country.  Two days of racing on Hambrooks Bay off the Choptank River. 10am to 5pm both days (weather permitting). Admission is FREE with a $5 a day charge for parking. Watch on land on bleachers at Gerry Boyle Park at Great Marsh.  Spectators can also watch the Cambridge Classic from their own boats on the water. The fleet will raft at Rooster Point. A no-wake zone will be established from Howell Point to the Choptank River Bridge.  Food and drinks will be available.  Gerry Boyle Park at Great Marsh, Cambridge, MD.

May 26 – 28, 2023 – 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 Party, Raft Race, Street Performances, Colonial Crafts, Strolling Musicians, Local Fare, 5k & 10 mile run. Chestertown, MD.