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.

  • Easton’s Annual Easter Egg Hunt

    Thousands of eggs will be spread out on the Talbot County Courthouse grounds on Saturday, April 8. Enjoy free face painting and an appearance by the Easter Bunny!

  • Taste of St. Michaels Tasting Crawl

    Taste of St. Michaels includes a Tasting Crawl on Saturday, April 15th from 11am – 4pm which allows participants to literally eat their way around the Town at award-winning restaurants. […]

  • Family Art Day – eARTh Arts Day Extravaganza!

    Make art together during these fun days for all ages! eARTh Arts Day Extravaganza! Saturday, April 22 10 am–1 pm FREE There is no cost to participate in Family Art […]

  • Easton Farmers Market (May 13th)

    From local produce growers to watermen, from bakers to crafters and local artisans, the Easton Farmers Market provides an entire meal, home décor and unique gift items in a friendly […]

    Free
  • Wine Tasting at St. Michaels Winery

    Wine tastings Hours Monday - Saturday (12pm-5pm) Sunday (12pm-4pm)  With 18 wines in our cellar, we have something for every pallet. Tasting Fee: $1.00 per wine sampled Glasses:  Glasses of […]

    $1
  • St. Michaels Farmer’s Market (20th)

      The St. Michaels Farmers Market features farmers and vendors selling locally grown and caught vegetables, meats, and fish, plus handmade crafts and live music.

    Free
  • 39th Annual Oxford Fine Arts Fair

    On Saturday and Sunday, the prestigious juried exhibit draws a wide selection of regional collectors as well as from major cities along the Eastern Seaboard. The much-anticipated annual show is […]

    $5
  • St. Michaels Farmer’s Market

    The St. Michaels Farmers Market features farmers and vendors selling locally grown and caught vegetables, meats, and fish, plus handmade crafts and live music.The St. Michaels Farmers Market features farmers […]

    Free
  • Classic Motor Museum Memorial Day Parade

    The CMM is proud to bring our community together in honoring the service of our military heroes by hosting the Annual Classic Motor Museum Parade. The participants will line up […]

    Free
  • St. Michaels Yacht Beer Tasting Cruise

    Available per person or Private Charter Join us for an unforgettable experience on our ice-cold Beer Tasting Cruises Be prepared for an unforgettable adventure on our beloved historic yacht Sail […]

    $115
  • St. Michaels Yacht Wine Tasting Cruise

    Enjoy a truly unforgettable wine tasting experience on the Chesapeake Bay with Sail Selina II. Our 2-hour St Michaels, MD wine tasting cruises are the perfect way to indulge in […]

    $115
  • Chesapeake Bay Champagne Sunset Sail

    Looking to go sailing at sunset while sipping champagne? This is the sunset champagne charter for you! Come join us for a relaxing 2 hour cruise near Annapolis. Your St […]

    $115