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.

  • Kent Island Farmers’ Market

    With over 30 local vendors at KENT ISLAND FARMERS’ MARKET at Cult Classic Brewery Year-round every Thursday. Hours 3:30- 6pm through Spring, Summer and Fall. January through March 3:30- 5:30. […]

    Free
  • Feasting Over Fire Series with Chesapeake Chefs

    Chestertown’s Brampton Inn and Chesapeake Chef Service are teaming up to present a series of alfresco dinner party’s highlighting the Eastern Shore’s farmers, watermen, cheesemakers, and many more. Reserve Your […]

  • Sea Witch Festival in Rehoboth

    Rehoboth Avenue 509 Rehoboth Beach, DE,19971, Rehoboth Beach, DE, United States

    About the Sea Witch® Festival The annual Sea Witch Festival is Rehoboth Beach’s free family-friendly Halloween celebration. Dress up and enjoy the parades, live entertainment, contests and more in downtown […]

  • Awww Shucks Oyster Harvest In Queenstown

    They will be shucking oysters all day long! More details as we get closer to the day. What pairs better with a briny, sweet oyster than an ice cold fresh […]

  • Queenstown Easter Egg Hunt

    Date/Time Date(s) - March 23, 2024 2:00 pm Venue Queenstown Community Park   Join us for the Queenstown Easter Egg Hunt on Saturday, March 23 at 2pm sharp at the […]

  • Kent Narrows Boat Expo

    3 Weekends to browse, tour and shop new and used boats.   The docks are connected from Safe Harbor Narrows South to Fisherman's Village with access to docks at Crab […]

  • Goat Yoga at Ten Eyck Brewing Co.

    Intimidated by Yoga? Scared to try a class out? What about if you don't take yourself so seriously + try a class...with GOATS! YES. You read that right. BABY GOATS. […]

  • Old School R&B Crab & Cruise in Crisfield

    Get ready for the ultimate seafood extravaganza of the summer! This event has premium crabs measuring 6 1/4" up to 8"! 97.5FM DJ, Big Mark will be mixing up the […]

  • Food Truck Night In Queenstown

    Food truck night supporting the Queenstown Volunteer Fire Department Auxiliary! Skip a night cooking and grab your dinner from one of our local vendors, starting at 4pm. Weather dependent, you […]