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.

  • 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 arranged seating areas, Epiphany provides the perfect setting for a relaxed and elevated wine tasting on the water. Guests can settle into abundant cushioned seating […]

  • 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 arranged seating areas, Epiphany provides the perfect setting for a relaxed and elevated craft beer tasting on the water. Guests can settle into abundant cushioned […]

  • Eastern Shore Sea Glass and Coastal Arts Festival

    Chesapeake Bay Maritime Museum 213 N Talbot St, St Michaels, MD, United States

    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 […]