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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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  • 21+ Cheers! Bingo Night in Cambridge

    Cambridge Moose Lodge 1211 would like to invite you to a fun CHEERS filled night of bingo. No one under 21 allowed. Prizes will included beer, wine, liquor and specials. […]

  • 10th Annual Sudlersville Peach Festival At Godfrey’s Farm

    Organizer: Event by Godfrey's Farm and Sudlersville Volunteer Fire Company Venue: Godfrey's Farm 302 Leager Rd, Sudlersville, MD 21668-1310, United States Date: August 2nd from 6pm to 9:30pm August 3rd […]

  • Ironman Course Group Ride in Cambridge

    Event by Tim Delss Cambridge-South Dorchester High School Come out and join us for a group ride of the IMMD bike course! That's right, we're back for another year so […]

  • 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 […]