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.

Looking for events near your rental? Browse vacation rentals by town.

Calendar of Events

Sunday
Monday
Tuesday
Wednesday
Thursday
Friday
Saturday
14 events,
17th annual St. Michaels Concours d’Elegance on Chesapeake Bay & 8th Annual Chesapeake Bay Motoring Festival
Easton’s Farmers Market
Easton Trivia Nights at Doc’s Downtown Grille
Old School R&B Crab & Cruise in Crisfield
First Friday of the Month Gallery Walk in Downtown Easton
Food Truck Night In Queenstown
Monthly Bingo in Easton
Emily’s Produce In Cambridge
Academy Art Museum in Easton
Tiger Lily Restaurant & Tiki Bar & More Summer Events
Talbot County Fair Celebrating 40 Years in Easton
Books And Beer At Cult Classic Brewing Company In Stevensville
Clipper ship Pride of Baltimore II In Cambridge
Skipjack Race & Festival
13 events,
Kent Island Farmers Market Fall Opening
14 events,
Emily’s Produce Harvest Celebration in Cambridge
14 events,
14 events,
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16 events,
57th Annual Maryland Seafood Festival in Annapolis
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15 events,
14 events,
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16 events,
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13 events,
14 events,
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14 events,
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12 events,
13 events,
Easton’s Fall Kickoff Weekend