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.

  • Tall Ship Kalmar Nyckel Sails in Cambridge (June 2nd)

    Come sail away with Kalmar Nyckel for a 2.5-hour sail and have an adventure of a lifetime! The Tall Ship of Delaware returns to Cambridge, MD on Friday, June 2 through Sunday, June 4. Discover the remarkable story behind Kalmar Nyckel, a full-scale replica of the merchant ship that brought Swedish settlers to North America […]

    $65
  • Tall Ship Kalmar Nyckel Sails in Cambridge (June 3rd)

    Come sail away with Kalmar Nyckel for a 2.5-hour sail and have an adventure of a lifetime! The Tall Ship of Delaware returns to Cambridge, MD on Friday, June 2 through Sunday, June 4. Discover the remarkable story behind Kalmar Nyckel, a full-scale replica of the merchant ship that brought Swedish settlers to North America […]

    $65
  • Sail on the Skipjack Nathan (June 3rd)

    Nathan sails from May through October. Each sail is two hours long and generally includes an oyster dredging demonstration. Sails are unique depending on wind, weather, captain and crew. Advance reservations are recommended and accepted online use the link below, until midnight of the day before the sail. We carry up to 20 passengers per […]

    $40
  • Tall Ship Kalmar Nyckel Sails in Cambridge (June 4th)

    Come sail away with Kalmar Nyckel for a 2.5-hour sail and have an adventure of a lifetime! The Tall Ship of Delaware returns to Cambridge, MD on Friday, June 2 through Sunday, June 4. Discover the remarkable story behind Kalmar Nyckel, a full-scale replica of the merchant ship that brought Swedish settlers to North America […]

    $65
  • Sail on the Skipjack Nathan (June 10th)

    Nathan sails from May through October. Each sail is two hours long and generally includes an oyster dredging demonstration. Sails are unique depending on wind, weather, captain and crew. Advance reservations are recommended and accepted online use the link below, until midnight of the day before the sail. We carry up to 20 passengers per […]

    $40
  • Sail on the Skipjack Nathan (June 17th)

    Nathan sails from May through October. Each sail is two hours long and generally includes an oyster dredging demonstration. Sails are unique depending on wind, weather, captain and crew. Advance reservations are recommended and accepted online use the link below, until midnight of the day before the sail. We carry up to 20 passengers per […]

    $40
  • Murder Mystery Dinner Cruise (June 17th)

    Take a relaxing 3-hour cruise and live show on one of the most exciting attractions offered on Maryland’s Eastern Shore! The boat offers a fully enclosed lower deck with heating and air conditioning, as well as a covered upper deck with a great view of the river. Catered by Suicide Bridge Restaurant and features local […]

    $85
  • Father’s Day Riverboat Cruise

    Take a relaxing 3-hour cruise on one of the most exciting attractions offered on Maryland’s Eastern Shore! The boat offers a fully enclosed lower deck with heating and air conditioning, as well as a covered upper deck with a great view of the river. Catered by Suicide Bridge Restaurant and features local seafood and Eastern […]

    $80
  • Sail on the Skipjack Nathan (July 1st)

    Nathan sails from May through October. Each sail is two hours long and generally includes an oyster dredging demonstration. Sails are unique depending on wind, weather, captain and crew. Advance reservations are recommended and accepted online use the link below, until midnight of the day before the sail. We carry up to 20 passengers per […]

    $40
  • Fireworks Near You 2023

    Add a little extra sparkle and excitement to your vacation with the local area's fireworks!  

    Free
  • July 4th Holiday Dinner Cruise

    Take a relaxing 3-hour cruise and dinner on one of the most exciting attractions offered on Maryland’s Eastern Shore! Followed by a beautiful display of fireworks!! The boat offers a fully enclosed lower deck with heating and air conditioning, as well as a covered upper deck with a great view of the river. Catered by […]

    $90
  • All You Can Eat July 4th Holiday Crab Cruise on the River Queen

    Cruise on one of the most exciting attractions offered on Maryland’s Eastern Shore… The Choptank Riverboat Company’s the Choptank River Queen paddle-wheeler. Ticket includes all you can eat Crabs, Maryland Crab Soup, Fried Chicken, Clam Strips, Corn on the Cob, Cole Slaw, Dessert, Non-Alcoholic Beverages. Followed by the fireworks around 9:45pm

    $90