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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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Talbot County

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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 […]

  • Kent Island Farmers Market Fall Opening

    Kent Island Farmers market is in their winter hours 3:30-6:00We are a year round farmers market! All vendors accept credit cards and or online payments POP UP VENDORS FOR THIS […]

  • 2 Hour Wine Tasting Cruise on Catamaran Epiphany

    Harbour Inn, 101 N Harbor Road, St Michaels MD

    Your Wine Tasting Experience Step aboard Epiphany, a spacious and stable modern catamaran designed for comfort, socializing, and panoramic Chesapeake Bay views. With her wide beam, open layout, and thoughtfully […]

  • Beer Tasting Cruises on Epiphany

    Harbour Inn, 101 N Harbor Road, St Michaels MD

    Your Beer Tasting Experience Step aboard Epiphany, a spacious and stable modern catamaran designed for comfort, connection, and panoramic Chesapeake Bay views. With her wide beam, open layout, and thoughtfully […]

  • Eastern Shore Sea Glass and Coastal Arts Festival

    Chesapeake Bay Maritime Museum 213 N Talbot St, St Michaels, MD, United States

    The Eastern Shore Sea Glass & Coastal Arts Festival will celebrate it's 16th Annual Spring Edition on the beautiful waterfront campus of the Chesapeake Bay Maritime Museum in St. Michaels […]

  • 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 […]