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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.

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Dorchester County

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  • 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, […]

    $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 […]

    $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 […]

    $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, […]

    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 […]

    $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 […]

    $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 […]

    $40