Events on Maryland’s Eastern Shore

Find upcoming events on Maryland’s Eastern Shore, including festivals, live music, arts and culture, food and drink events, and seasonal celebrations. This local events calendar highlights what’s happening in Easton, St. Michaels, Oxford, Chestertown, and nearby Eastern Shore towns, making it easy for visitors and residents to plan their time in the area.

Looking for events near your rental? Browse vacation rentals by town.

Loading Events

« All Events

  • This event has passed.

2024 Cambridge Classic Powerboat Regatta

May 18, 2024 @ 10:30 am - May 19, 2024 @ 5:00 pm

Racing since 1911, the oldest active powerboat race in the country happens right here in Dorchester County, Maryland. This year’s race will be held on May 18-19, 2024 on the Choptank River. About 70 boats are expected to be on hand to create an exciting two days of racing. Admission is FREE with a $5 a day charge for parking. Kid’sZone, Food, and drinks will be available.
Brought to by the Hydroplane Racing League (HRL), the Cambridge Power Boat Racing Association (CPBRA), and the Dorchester Chamber of Commerce. Learn more by visiting our website: https://cpbra.com/

Venue: Great Marsh Park, Cambridge, MD, United States, Maryland 21613

Details

Details