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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  • 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 Day Monday, Sept. 2. As always, the Island Fest on both Sunday and Monday offers a variety of events—parade, live music, car show, blessing of […]

  • 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 vendors, food, moon bounce, music, 50/50 raffle & lots of fun!

  • 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 opening weekend of our 2024 corn maze!! We'll be opening the pumpkin patch & the corn maze, we'll have so many yummy fall treats (apple […]

  • 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 a two day Fall celebration! Website: https://discovereaston.com/fallkickoff/ Stay tuned for more details! FRI, OCT 4th  AT 4 PM to 9:45PM Sat, OCT, 5th AT 10AM to […]

  • 53rd Annual Waterfowl Festival In Easton

    Join for a family-friendly festival celebrating the waterfowl, outdoor spaces, and wildlife of the Eastern Shore!   Incredible Art, music, food, shopping, dog field trials, duck calling contest, dock dog contests, and so much more!   Venue: 40 S Harrison St, Easton, MD 21601-3019, United States   Organizer:   Event by Waterfowl Festival

  • Easton’s 1st Christmas Vendor & Craft Fair at the American Legion

    Come out to the American Legion Post 70 for their first (hopefully) annual vendor and craft fair! Proceeds from this event will help the Post’s mission of helping veterans, their families and the community through various programs. Tables for vendors are $20 and on a first come basis. To reserve your spot please contact Kaki […]

  • Amish Country Farmer’s Market

    Amish Country Farmers Market every Thursday through Saturday – indoor market offering fresh produce, meats, dairy products, furniture, handcrafted items, and indoor and take away dining and more! Thurs 9 AM – 6 PM; Fri 9 AM – 7 PM & Sat 9 AM – 3 PM. Easton Plaza, 101 Marlboro Avenue, Easton. 410-822-8989.

  • Academy Art Museum

    Academy Art Museum – Permanent Collection contains more than 1,000 pieces including core holdings of European and American works on paper. Academy Art Museum, 106 South Street, Easton. Tue & Wed 10 AM – 4 PM; Thurs 10 AM – 6 PM; Fri 10 AM – 7 PM; Sat & Sun 10 AM – 4 PM. […]