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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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Today

  • Food Truck Night In Queenstown

    Food truck night supporting the Queenstown Volunteer Fire Department Auxiliary! Skip a night cooking and grab your dinner from one of our local vendors, starting at 4pm. Weather dependent, you […]

  • 2 Hour Wine Tasting Cruise on Catamaran Epiphany

    Harbour Inn, 101 N Harbor Road, St Michaels MD

    Your Wine Tasting Experience Step aboard Epiphany, a spacious and stable modern catamaran designed for comfort, socializing, and panoramic Chesapeake Bay views. With her wide beam, open layout, and thoughtfully arranged seating areas, Epiphany provides the perfect setting for a relaxed and elevated wine tasting on the water. Guests can settle into abundant cushioned seating […]

  • Beer Tasting Cruises on Epiphany

    Harbour Inn, 101 N Harbor Road, St Michaels MD

    Your Beer Tasting Experience Step aboard Epiphany, a spacious and stable modern catamaran designed for comfort, connection, and panoramic Chesapeake Bay views. With her wide beam, open layout, and thoughtfully arranged seating areas, Epiphany provides the perfect setting for a relaxed and elevated craft beer tasting on the water. Guests can settle into abundant cushioned […]

  • Paint The Town Show + Sale

    343 High Street, Chestertown MD 21620

    🎨✨ Paint the Town: Art Show & Sale ✨🎨 Get ready to celebrate creativity at Paint the Town, our exciting art show and sale featuring local artists! Discover vibrant paintings, unique prints, and one-of-a-kind works — all available to take home and support local talent. Whether you’re an art collector, a casual admirer, or looking […]

  • 𝐁𝐥𝐨𝐨𝐦 & 𝐁𝐫𝐮𝐧𝐜𝐡

    Kent Island Resort

    🌸 𝐁𝐥𝐨𝐨𝐦 & 𝐁𝐫𝐮𝐧𝐜𝐡🌸 𝐎𝐮𝐫 𝐌𝐨𝐭𝐡𝐞𝐫’𝐬 𝐃𝐚𝐲 𝐂𝐫𝐞𝐚𝐭𝐢𝐯𝐞 𝐁𝐫𝐮𝐧𝐜𝐡 𝐢𝐬 𝐛𝐚𝐜𝐤 If you’re looking for something meaningful (and not just another crowded restaurant brunch), this is it. Join us at Kent Island Resort Garden Room for a creative brunch experience you’ll actually remember. ✨ You’ll create a pressed flower & butterfly resin keepsake ✨ Enjoy […]

  • Resin Wave Board Workshop

    El Jefe Mexican Kitchen/Tequila Bar

    Bring a touch of seaside charm into your home! In this relaxing and creative workshop, you’ll learn the art of mixing, pouring, and layering resin to create stunning ocean wave effects. With multiple board shapes and sizes to choose from, your project will be as unique as you are. These pieces make beautiful décor for […]

  • Chesapeake Chamber Music Festival

    Ebenezer Theater

    Where Artists, Audiences, and Acoustics Come Together in Downtown Easton, Maryland! The Chesapeake Chamber Music Festival, now in its 41st year, is held over the course of two-weeks each June at the beautifully restored Ebenezer Theater in downtown Easton. It is a celebration of the ensembles that take on varied periods and styles of music.

  • Plein Air Easton (PAE)

    Waterfowl Headquarters (40 S Harrison St.)

    When is Plein Air Easton? The annual competition is held in Easton, Maryland, each July. 2026 Plein Air Easton is planned for July 10-19, 2026. What is Plein Air Easton? Each year, a unique juror selects 58 artists to participate. Artists apply from around the world for a chance to compete at the prestigious event. […]

  • Chesapeake Film Festival

    Ebenezer Theater, Academy Art Museum, and Talbot County Free Library

    Talbot County has found itself starring on the big screen from time to time, but this Oct. 8-10, 2026 the film industry becomes the star in Talbot County as it gears up for one of the most exciting cultural events of the year – the Chesapeake Film Festival. Whether you’re a cinematic extraordinaire or just […]