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.

  • Easton’s Fall Kickoff Weekend

    Event by Discover Easton Venue: 11 S Harrison St, Easton, MD, United States, Maryland 21601 Autumnal decorations and the feeling of seasonal warmth will be all around downtown Easton for […]

  • 53rd Annual Waterfowl Festival In Easton

    Join for a family-friendly festival celebrating the waterfowl, outdoor spaces, and wildlife of the Eastern Shore!   Incredible Art, music, food, shopping, dog field trials, duck calling contest, dock dog […]

  • Amish Country Farmer’s Market

    Amish Country Farmers Market every Thursday through Saturday – indoor market offering fresh produce, meats, dairy products, furniture, handcrafted items, and indoor and take away dining and more! Thurs 9 AM […]

  • Talbot Historical Society Museum

    Talbot Historical Society Museum – Approximately 1000 vintage photos tell the fascinating story of Talbot County and its people. Award-winning formal gardens are open daily. Exhibit Wednesdays through Saturday, 10 AM […]

  • Academy Art Museum

    Academy Art Museum – Permanent Collection contains more than 1,000 pieces including core holdings of European and American works on paper. Academy Art Museum, 106 South Street, Easton. Tue & Wed […]