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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  • Saint Patrick’s Day Parade

    Each year Easton celebrates Irish heritage during our St. Patrick’s Day festivities! The Easton Saint Patrick's Day Parade starts at 5:30 p.m. and features over 40 floats, bands, classic cars, and local businesses. The Annual Potato Races take place downtown immediately following the parade. Come celebrate with us on Saint Patrick's Day.

  • 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. Each tasting venue will have tasting selections that feature food and drinks, Chesapeake Bay inspired. Tastings can be purchased, ranging from $1-$5, at participating venues […]

  • 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 Days, but please let AAM know if you are coming, as it will help them plan. Sign up online!

  • 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 and festive environment. The market is open every Saturday from April 15 to December 16, 2023 at 8 a.m. to 1 p.m. Live music starts […]

    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 well known throughout the area and celebrated as the season’s “kick-off” for art lovers. The exhibit featuring 36 artists from the mid-atlantic region and beyondis […]

    $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 at Perry Cabin Park, and will head down Talbot St, pausing near Railroad Avenue for the emcee to announce the make, model, and driver of […]

    Free