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.

  • Downtown Easton’s 4th of July Sidewalk Sale

    Join our downtown retailers as they clear out their racks and make room for new inventory at the 4th of July Sidewalk Sale! This annual sale always offers BIG savings […]

  • Blooms and Brews @ Corah’s Corner and more Summer Events

    Join us for a fun blooms and brew experience. Arrange beautiful local flowers while tasting local brews on Corah’s beautiful deck! NOTE: This event is July 19. Tickets: https://l.facebook.com/l.php?u=https%3A%2F%2Fwww.vintagefamilyfarms.com%2Factivities%3Ffbclid%3DIwZXh0bgNhZW0CMTAAAR29aRbzkisG7updQs8W6QwoQUuiDjQtpqsZEgMuzZwBNf_BUk6WixpR4Sg_aem_jaPb6rlFwyuLZL6_3EYVYA&h=AT2LZZbtn1QPXSHUoCX1GnfTdX1ulC0dUqQ-z3FEkpUZHwcqG55dXfEE_BfCoc-V059f-1Nx9ja7YURUXB57yPQXZsvb3yx7HUieILJB8-fI7R8sY9MFm1Ob2OaNq2vTUrKexIJxiATtQRTv2I74DUJ-3GI Event […]

  • Planes – Outdoor Movie Night at The Easton Airport

    Bring a chair and a blanket for cinema at the airport! Our movie nights will be a free event for all ages. Venue: 29051 Corkran Rd, Easton, MD 21601-7063, United States Event by Discover Easton and Easton Airport

  • Talbot County Fair Celebrating 40 Years in Easton

    The Talbot County Fair is held every year during the second week in July. It is open to the public. Lots of Fun, Food, Entertainment and More!! For more information, […]

  • Pinot on the Patio in St. Michaels

    Join us for a weekend of everything Pinot! Friday night - a multi-course dinner by Stephanie Cook, chef and owner of Wonderment Wines. Saturday - enjoy an afternoon tasting on the patio with some of the best Pinots! Join us for dinner at $100 per person or Saturday tasting at $50. We welcome our beloved […]