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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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Today

  • The Berlin Farmers Market

    Only market in the heart of downtown Berlin featuring more than 30 farmers, bakers, food cultivators and more. Shops in the downtown also open early on Sundays. Live music starts […]

    Free

  • Waterfront Wine & Jazz Dinner

      Guest( 10 per table) will be greeted with a choice of our sparkling Rosés, Slipstream or Moondance(new), while you settle in, laugh with friends, and feel your entire self […]

    $175

  • Delmarva Pride Festival

    Delmarva Pride 2023 Delmarva Pride takes place over the weekend 16th to 18th June 2023.

  • Delmarva Pride Presents 2nd Annual Drag Show

    If you attended last year’s event, you know this show is going to be a wonderful night of entertainment fit for a queen! As part of its Annual Pride Weekend, […]

    $20 – $30

  • Annapolis Juneteenth Parade & Festival

    Come out and join us for our FREE 2nd annual parade and festival on Saturday, June 17, 2023! There will be TWO main stages this year, featuring headliners Avery*Sunshine, Koryn […]

    Free

  • 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 […]

    $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 […]

    $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, […]

    $80

  • St. Michaels Ghost Walk – Spirits of Rowdy Women

    The walk begins in front of the Chesapeake Bay Maritime Museum and makes its way through around the St. Michaels harbor and around St. Michaels historic downtown. Visit an old […]

    $25

  • 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

  • Special 4th of July Fireworks Cruise

    Saturday July 2, 2022 8 PM to 10 PM, $150 per person plus tax and gratuity. Join us for the ultimate Independence Day celebration and Sail Selina the Ultimate St […]

    $150