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.

  • 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
  • 4th of July & fireworks in Cambridge

    Celebrate Independence Day on the Cambridge waterfront with fireworks over the Choptank River!  The best fireworks viewing is at Gerry Boyle Park at Great Marsh, 1 Somerset Ave. in Cambridge, MD. And at Long Wharf Park, High and Water Streets in Cambridge. Fireworks generally start at dusk, around 9:15pm. Bring your own chairs or blankets […]

    Free
  • Summer Music at Blue Ruin Cocktail Bar & Restaurant

    Offers small plates with intense flavors and specializes in over 150 different kinds of cocktails! Join Blue Ruin for live music on these dates! July 14th - Bryan Russo 8-10pm […]

    Free
  • Sail on the Skipjack Nathan (July 15th)

    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 (July 15th)

    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
  • Sail on the Skipjack Nathan (July 22nd)

    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