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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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  • 5th Annual EycktoberFest in Queenstown

    Join us for our 5th Annual EycktoberFest! YOU have made this event our favorite every year! German-inspired eats by Field Kitchen! Games of skill including the Stein Hoist, Hammerschlagen and […]

  • Dinner & Dance at the American Legion in Cambridge

    All Proceeds will be used to support our Veteran Programs! Dinner 6:00PM - Spaghetti, Salad, Bread and Dessert.Music 7:00PM - Featuring Double Nickels!Silent Auction Table and 50/50 Raffles! Advance Tickets are $18 or $20 at the Door.For tickets or to reserve a table, please call 410.463.1281 Event by Dorchester Post 91 American Legion Venue: 98 […]

  • All-You-Can-Eat Seafood Extravaganza

    Date and time   Wednesday, September 25 · 11:30am - 3pm EDT Location   Somers Cove Marina 715 Broadway Ave Crisfield, MD 21817 Show map Refund Policy Refunds up to […]

  • Chefs Table Seafood Night in Stevensville

    Event by Kent Island Resort Venue: 500 Kent Manor Drive, Stevensville, MD, United States, Maryland 21666 Tickets · $103.22 www.eventbrite.com/e/chefs-table-seafood-night-tickets-942553020457 C Join us for Chef's Table, featuring a curated menu […]

  • Easton’s Fall Kickoff Weekend

    Event by Discover Easton Venue: 11 S Harrison St, Easton, MD, United States, Maryland 21601 Autumnal decorations and the feeling of seasonal warmth will be all around downtown Easton for a two day Fall celebration! Website: https://discovereaston.com/fallkickoff/ Stay tuned for more details! FRI, OCT 4th  AT 4 PM to 9:45PM Sat, OCT, 5th AT 10AM to […]

  • 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 […]

  • 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? […]