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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, 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 is […]

    Free

  • Easton Farmers Market (May 13th)

    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

  • Blackwater Refuge Wildlife Drive

    The 4-mile long Wildlife Drive is open from sunrise to sunset every day, takes you through several types of wildlife-rich habitat found at Blackwater National Wildlife Refuge.   Wildlife Drive […]

    $3

  • Emily’s Produce

    The market with a U-Pick strawberry, blackberry, blueberry and cherry patch, U-Cut flower patch, and a beautiful selection of hanging baskets, perennials, annuals, and planters straight from their own greenhouse. […]

    Free

  • Wine Tasting at St. Michaels Winery

    Wine tastings Hours Monday - Saturday (12pm-5pm) Sunday (12pm-4pm)  With 18 wines in our cellar, we have something for every pallet. Tasting Fee: $1.00 per wine sampled Glasses:  Glasses of […]

    $1

  • Old Courthouse Distillery

    Once the oldest working courthouse in Maryland now currently the Old Courthouse Distilling was established in 2019! Distillery Hours Wednesday - 3:00pm to 9:00pm Thursday - 3:00pm to 9:00pm Friday […]

    $10

  • Kent Island Farmers’ Market (May 18th)

    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

  • Cambridge Classic Powerboat Regatta

    The oldest active powerboat race in the country happens right here in Dorchester County, Maryland. This year's race will be held on May 20-21, 2023 on the Choptank River. About […]

  • St. Michaels Farmer’s Market (20th)

      The St. Michaels Farmers Market features farmers and vendors selling locally grown and caught vegetables, meats, and fish, plus handmade crafts and live music.

    Free

  • 39th Annual Oxford Fine Arts Fair

    On Saturday and Sunday, the prestigious juried exhibit draws a wide selection of regional collectors as well as from major cities along the Eastern Seaboard. The much-anticipated annual show is […]

    $5