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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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Easton

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  • Pinot on the Patio in St. Michaels

    Join us for a weekend of everything Pinot! Friday night - a multi-course dinner by Stephanie Cook, chef and owner of Wonderment Wines. Saturday - enjoy an afternoon tasting on […]

  • Clipper ship Pride of Baltimore II In Cambridge

    Head to Cambridge, Md. Labor Day weekend to see the glorious replica clipper ship Pride of Baltimore II. Dock tours, day sails, sunset sails, Aug. 31 to Sept. 2. Details. […]

  • Skipjack Race & Festival

    Festival Grounds includes Food Vendors, Arts & Crafts Vendors, Heritage & Education Exhibits and free Children's Activities, both Sunday and Monday The Deal Island (Md.) Skipjack Races happen on Labor […]

  • Labor Day Parade in Grasonville

    Event by Grasonville Community Center Grasonville Community Center Monday September 2nd 5601 Main Street, Grasonville MD Parade starts at 12pmLine up starts at 10am Following the parade there will be […]

  • Emily’s Produce Harvest Celebration in Cambridge

    Who's ready for Fall on the farm?? WE ARE!! Come kick start your Fall season with us at our Harvest Celebration-it's the OFFICIAL start of Autumn at Emily's and the […]

  • Councell Farms Opening Day near Easton

    Councell Farms Opening Day! Come visit the Field of Fun, market and get our farm fresh ice cream! Open daily 9:30-5:30 until October 30th. Event by Councell Farms Venue: 11773 Old Skipton Rd, Cordova, MD

  • Annual End of Summer Crab, Bull, and Oyster Roast In Grasonville

    Join us for our annual End of Summer Crab, Bull, and Oyster Roast! Enjoy crabs, oysters, pit beef, pulled pork, corn on the cob, coleslaw, domestic beer, wine, and seltzers, along with live music! Don't miss out, as this event sells out every time Event by Jetty Dock Bar 201 Wells Cove Rd, Grasonville, MD, […]

  • 5th Annual EycktoberFest in Queenstown

    Join us for our 5th Annual EycktoberFest! YOU have made this event our favorite every year! German-inspired eats by Field Kitchen! Games of skill including the Stein Hoist, Hammerschlagen and Beer Puppeteer! Commemorative beer steins! We will have the full Edelweiss Band performing 2-5PM! It’s a full day of celebration, 12-10PM Details Date: September 21 […]

  • Easton’s Fall Kickoff Weekend

    Event by Discover Easton Venue: 11 S Harrison St, Easton, MD, United States, Maryland 21601 Autumnal decorations and the feeling of seasonal warmth will be all around downtown Easton for […]

  • Chesapeake Chamber Music Festival

    Ebenezer Theater

    Where Artists, Audiences, and Acoustics Come Together in Downtown Easton, Maryland! The Chesapeake Chamber Music Festival, now in its 41st year, is held over the course of two-weeks each June […]

  • Plein Air Easton (PAE)

    Waterfowl Headquarters (40 S Harrison St.)

    When is Plein Air Easton? The annual competition is held in Easton, Maryland, each July. 2026 Plein Air Easton is planned for July 10-19, 2026. What is Plein Air Easton? […]