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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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  • Easton’s Farmers Market

    The Easton Maryland Farmers Market has been operating for over 40 years. Located in the municipal parking lot in the 100 block of North Harrison Street the pedestrian-only market features […]

  • Easton Trivia Nights at Doc’s Downtown Grille

    Let's Do Trivia! is a weekly, team-based, live-hosted pub and restaurant trivia game show. FRIENDS * FOOD * FUN! FREE TO PLAY - BIG PRIZES TO WIN! $40 First Place […]

  • Monthly Bingo in Easton

    Lunch available doors open at 12 Venue: 29511 Canvasback Dr, Easton, MD 21601-7141, United States Event by George Willey

  • Academy Art Museum in Easton

    WHERE ART IS FOR EVERYONE Welcome to the Academy Art Museum! Plan your visit with us and discover something new. OPEN TODAY 10:00 AM  - 7:00 PM | FREE ADMISSION EVERY […]

  • Tiger Lily Restaurant & Tiki Bar & More Summer Events

    the KG Band will be rockin' Tiger Lily again. Come dance and listen to some of your favorite Classic Rock tunes while you enjoy the awesome Tiger Lily Tiki Bar. […]

  • 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 […]

  • 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? […]

  • Chesapeake Film Festival

    Ebenezer Theater, Academy Art Museum, and Talbot County Free Library

    Talbot County has found itself starring on the big screen from time to time, but this Oct. 8-10, 2026 the film industry becomes the star in Talbot County as it […]