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 Carriage Tours

    VALENTINE'S DAY 2024 NOW OPEN FOR BOOKINGNew this year: We are partnering with Tiger Lily for the ultimate Valentine's experience! Have a romantic carriage ride around Easton followed by dinner ON US at Tiger Lily! ​ Riding and Driving lessons can be booked by clicking BOOK NOW. Please email [email protected] or text 540-460-2455 for private rentals and driving lessons. […]

  • Far Eastern Shore Winery’s – Sip and Stitch Sundays

    About this event Far Eastern Shore Winery invites you to join us for our Sip & Stitch Sundays series. We’ve had so much fun the past two Sip & Stitch Events over Halloween weekend and, more recently, on Small Biz Saturday, we thought we’d try to grow our stitching network. We’ll be hosting informal crochet […]

  • 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 […]

  • 4th Annual Breakfast with the Easter Bunny

    The Galley Restaurant, L.L.C. 305 S Talbot Street, Saint Michaels, MD, United States

    This Easter, embark on a delightful journey filled with joy and wonder alongside your little ones at The Galley Restaurant's enchanting Breakfast with the Easter Bunny event! Check out the […]

    $38
  • Annual Easter Egg Hunt In Easton

    Thousands of eggs will be spread out on the Talbot County Courthouse grounds on Saturday, March 30, along with a special appearance by the Easter Bunny! DETAILS Date: March 30 […]

  • 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 […]

  • 8th Annual St. Michaels Sea Glass Festival Expands

    Chesapeake Bay Maritime Museum 213 N Talbot St, St Michaels, MD, United States

    The 8th annual Eastern Shore Sea Glass and Coastal Arts Festival in St. Michaels, Md. will now have a larger, waterfront location at the Chesapeake Bay Maritime Museum (CBMM). The Sea […]

  • Kent Narrows Brew Fest In Grasonville

    Attention beer enthusiasts! HOPS into Spring  at the Kent Narrows Brew Fest! This is a 21+ event. General Admission tickets are $50. Designated Driver tickets are $20. Tickets: https://kentnarrowsbrewfest.ticketleap.com/?fbclid=IwAR3mydSgN8kVIOX2dMtbJWqNVnjip3NLK5Y4faFWxIwv8osGMKHqM_f9qec Come […]

  • 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, […]