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.

  • Kent Narrows Boat Expo

    3 Weekends to browse, tour and shop new and used boats.   The docks are connected from Safe Harbor Narrows South to Fisherman's Village with access to docks at Crab […]

  • Sea Glass Crab Workshop at Alibi Gastropub

    Sunday April 14 4-6pm Tickets: $46 Join us for a fun creative evening at Alibi Gastropub in Centreville to create our newest piece. We will be using paint and tumbled […]

  • Taste Of St. Michaels

    Town of St. Michaels 101 N Harbor Rd, St.Michaels, MD, United States

    Come Hungry...Leave Happy! Taste Of St. Michaels includes a tasting crawl on Saturday, April 15th from 11 am - 4 pm.   The Tasting Crawl allows participants to taste their way around St. […]

  • Tequila and Tulips

    Vintage Family Farms and Corah's Corner are teaming up again to bring you a create your own Tulip bouquet bar with our own field grown Tulips and your favorite Tequila […]

  • The Eastern Shore Sea Glass and Coastal Arts Festival

    The Eastern Shore Sea Glass and Coastal Arts Festival brings artisans and craftspeople who will exhibit and sell coastal and sea-glass related jewelry, home décor, art, and more. The popular […]

  • Chesapeake Bay And Maryland Eastern Shore Bike Tour

    Delight for four relaxing days in the food, history, and culture of Maryland's Chesapeake bay! You will ride along the historic Eastern Shore with the perfect mix of easy riding […]

  • Talbot County Day

    Join us on the Talbot County Courthouse Lawn on April 25th, 2024 at 5PM as we celebrate the birthday of Talbot County. This special birthday celebration will include music from […]

  • First Annual CMS Spring Thing

    Free Community Event. Food Trucks, Live Music, Emergency Equipment, Non-Profit Booths, Vendor Fair, and more! Venue: Centreville Middle School Event by Thomas Hayman and Centreville Middle School

  • VIP WineFest 2024

    Old Brick Inn Properties 401 S. Talbot, St. Michaels, MD, United States

    VIP WineFest 2024 We are pleased to announce WineFest 2024! We are bringing back WineFest 2024. Wine will be tasted from many countries around the world! Wine will be poured, […]