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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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  • 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

  • Feasting Over Fire Series with Chesapeake Chefs

    Chestertown’s Brampton Inn and Chesapeake Chef Service are teaming up to present a series of alfresco dinner party’s highlighting the Eastern Shore’s farmers, watermen, cheesemakers, and many more. Reserve Your […]

  • Kent Narrows Brew Fest In Grasonville

    Attention beer enthusiasts! HOPS into Spring  at the Kent Narrows Brew Fest! This is a 21+ event. General Admission tickets are $50. Designated Driver tickets are $20. Tickets: https://kentnarrowsbrewfest.ticketleap.com/?fbclid=IwAR3mydSgN8kVIOX2dMtbJWqNVnjip3NLK5Y4faFWxIwv8osGMKHqM_f9qec Come […]

  • Kent Narrows Boat Expo

    3 Weekends to browse, tour and shop new and used boats.   The docks are connected from Safe Harbor Narrows South to Fisherman's Village with access to docks at Crab […]

  • Bull Roast at Grasonville’s VFW

    Food, Corn-hole, and much more start at 3 the fabulous Kick Back Band will start playing around 6 Tickets are available for Purchase at the VFW 410-827-8194   Venue: Grasonville […]

  • Cinco De Mayo at The Jetty Dock Bar in

    Celebrate Cinco de Mayo with us at The Jetty Dock Bar! We’ll be serving up all your favorite rock and dance hits from the 90’s and 2000’s!   Event by […]

  • Old School R&B Crab & Cruise in Crisfield

    Get ready for the ultimate seafood extravaganza of the summer! This event has premium crabs measuring 6 1/4" up to 8"! 97.5FM DJ, Big Mark will be mixing up the […]

  • 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!

  • Rockfish Rodeo Fishing Tournament and Crab Feast in Grasonville

    2024 Rockfish Rodeo Fishing Tournament and Crab Feast Benefitting Talisman Therapeutic RidingSeptember 9, 2024All Boats Launch from Fisherman's Crab Deck at 6:00 AM Sign Up Now:Sponsorships Available!Single Anglers - $225 […]