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.

All Day

2 Hour Wine Tasting Cruise on Catamaran Epiphany

Harbour Inn, 101 N Harbor Road, St Michaels MD

Your Wine Tasting Experience Step aboard Epiphany, a spacious and stable modern catamaran designed for comfort, socializing, and panoramic Chesapeake Bay views. With her wide beam, open layout, and thoughtfully […]

Beer Tasting Cruises on Epiphany

Harbour Inn, 101 N Harbor Road, St Michaels MD

Your Beer Tasting Experience Step aboard Epiphany, a spacious and stable modern catamaran designed for comfort, connection, and panoramic Chesapeake Bay views. With her wide beam, open layout, and thoughtfully […]

Eastern Shore Sea Glass and Coastal Arts Festival

Chesapeake Bay Maritime Museum 213 N Talbot St, St Michaels

The Eastern Shore Sea Glass & Coastal Arts Festival will celebrate it's 16th Annual Spring Edition on the beautiful waterfront campus of the Chesapeake Bay Maritime Museum in St. Michaels […]