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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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  • Cambridge Farmers’ Market

    Operating May through November in 2023, Every Thursdays from 3pm – 6pm, the Long Wharf Farmer’s Market is a local favorite!  What’s better than a waterfront Farmer’s Market? The market […]

    Free

  • St. Michaels Yacht Beer Tasting Cruise

    Available per person or Private Charter Join us for an unforgettable experience on our ice-cold Beer Tasting Cruises Be prepared for an unforgettable adventure on our beloved historic yacht Sail […]

    $115

  • St. Michaels Yacht Wine Tasting Cruise

    Enjoy a truly unforgettable wine tasting experience on the Chesapeake Bay with Sail Selina II. Our 2-hour St Michaels, MD wine tasting cruises are the perfect way to indulge in […]

    $115

  • Chesapeake Bay Champagne Sunset Sail

    Looking to go sailing at sunset while sipping champagne? This is the sunset champagne charter for you! Come join us for a relaxing 2 hour cruise near Annapolis. Your St […]

    $115

  • Easton Farmers Market

    From local produce growers to watermen, from bakers to crafters and local artisans, the Easton Farmers Market provides an entire meal, home décor and unique gift items in a friendly […]

    Free

  • 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 […]

    $40

  • St. Michaels Brewfest 2023

    On June 3rd, from 12:00 pm - 4:00 pm come out to the St. Michaels Brewfest 2023! They offer Three Pouring Venues, Over A Dozen Breweries, Art, Glassware, Food, and […]

    $55 – $110

  • Annapolis Pride Parade & Festival

    With over 6,000 people in attendance, 2019 launched the Inaugural Annapolis Pride Parade & Festival– a visual dreamscape of the human spirit at its best. People, children, and pets of every […]

    Free

  • 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