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.

  • Cars and Coffee in the Barn Classic Motor Museum Saturdays

    Motor Museum 102 E. Marengo Street, St. Michaels, MD, United States

    Hosted by: Classic Motor Museum St Michaels Where: 102 E. Marengo Street, St. Michaels Maryland. When: Every Saturday Morning  9 am to 11 am. From now through the end of March we have […]

  • Build-Your-Own Bloody Mary/Maria Bar at The Fool’s Lantern

    The Fool's Lantern 310 S. Talbot St., St.Michaels, MD, United States

    Join us every Saturday and Sunday at The Fool's Lantern for brunch and our Build-Your-Own Bloody Mary/Maria Bar! Choose from a variety of vodka or tequila, add our house made […]

  • Simpatico Free Wine Tasting Events Every Weekend

    Simpatico 104-106 Railroad Ave, St.Michaels, MD, United States

    top by Simpatico's Courtyard or in the Shop at 104-106 Railroad Ave, just off Talbot Street, every weekend for free tastings of our hand-picked Italian wines! Peruse the shop and […]

  • Corah’s Corner Annual Easter Brunch In St. Michaels

    Come and join Corah's Corner for our Annual Easter Brunch! We will have a Special Easter Brunch menu, a special kiddo menu, Bottomless Mimosas & Bloody Mary’s, Fun Craft Cocktail and More!!! LIVE Music with Sam Pugh starting at 11am!!!  Reservations Preferred 410-745-8008 Venue: 105 N Talbot Street, Saint Michaels, MD Event by Corah's Corner

  • Corah’s Corner Easter Brunch W/ Easter Bunny In St. Michaels

    Corah's Corner will have Easter Brunch on Sunday, April 9th from 10am-3:30 pm- The Easter Bunny Brunch portion for the kiddos will be from 10-12 am! Parents! Here’s your photo opportunity!!!! It’s going to be our BEST, most delicious Easter Brunch yet!!!! Reserve spot: 410-745-8008 Venue: 105 N Talbot Street, Saint Michaels, MD

  • Annual Multicultural Festival in Easton

    Save the date! The Avalon Foundation’s Annual Multicultural Festival returns to Easton’s Idlewild Park with a fun day of diverse musical traditions, arts, and food on Saturday, May 4, 2024, […]

  • Spring Paint & Sip

    Spring is in the air, and brighter days are ahead. Looking for a fun excuse to get out of the house? Well, look no further. Far Eastern Shore Winery will […]

  • 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 […]

  • 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 […]