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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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Dorchester County

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  • Oktoberfest in Berlin

    Berlin Oktoberfest & Sidewalk Sale 2 Bands! Authentic Oktoberfest music featuring The Edelweiss Band! Plus local favorite The Dunehounds perform sponsored by The Sterling Tavern Cascading Carlos Juggling Shows – Scales […]

  • Talbot County Fall Harvest Fair

    Talbot Agricultural Center 10659 Hiners Lane, Easton, MD, United States

    🌾 2023 Fall Harvest Fair - Celebrate the Season with Us! 🌾 Join us for a day of wholesome fun and community spirit at the Fall Harvest Fair on Sunday, October 15th, […]

  • Ice Ice Berlin and Tree Lighting

    Join us as we begin the holiday season featuring beautifully carved Ice Sculptures sponsored by the Berlin businesses! 30+ Holiday themed lighted sculptures Tree is lit at 6pm Greet Santa at Kringle Kottage at the Taylor House Museum Music by DJ Big Al Reno  – Shops open late!

  • Berlin New Years Eve Celebrations

    Celebrate New Years eve in Berlin with two ball drops. One for the kids at 6pm and the other at midnight. Laser shows, dancing and more. Free to attend and park.

  • Valentines’s Cookie Class Part of the Cookie Classes collection

    About this event Sunday, February 4 · 12 - 1:30pm EST 1 hour 30 minutes Mobile eTicket Valentine's Cookie Class Join us for a fun and delicious Valentine's Cookie Class at Carrie Sue’s CupCakery! Get your hands dirty and learn the art of decorating cookies with our Brandy from Shore Good Cookies. This in-person event will […]

  • 411 kitchen winter dining experience

    Join us for an unforgettable dining experience at Layton’s Chance Vineyard & Winery. Indulge in a delectable culinary journey prepared by our talented chef Chris, showcasing the finest ingredients and flavors. Immerse yourself in the cozy ambiance of the vineyard, surrounded by breathtaking views and the soothing sounds of nature. Savor each bite as you […]

  • Spring Vendor Market In Cambridge

    Join on April 6th from 9am- 1pm Lots of vendors including Scentsy, tastefully simple, thirty one, Tupperware, paintings, jewelry, tumblers, wreaths, leather goods, signs, cupcakes, country decor, handmade items, candles, bath salts and lots more. The Auxiliary will also be serving breakfast and lunch during the Event. Hope to see you there. Please come out […]

  • St. Pat’s Karaoke Night @ Lil’ Bitta Bull

    Join Leprechaun Lucky Chuckie as we kick off St. Patrick's weekend! Friday Night Karaoke starts at 9 p.m. at Lil' Bitta Bull BBQ and going until... $5 Lucky Shots all night! Kitchen […]

  • 20th Annual Eagle Festival

    The 20th Annual Eagle Festival at Blackwater National Wildlife Refuge on Saturday, March 16, 2024, from 9:00 a.m. to 4:00 p.m. as we celebrate birds of prey! Don’t miss out […]

  • Cambridge Rotary Community Foundation Oyster Festival

    Join us for a shuckin' good time at the Cambridge Rotary Community Foundation Oyster Roast! Indulge in delicious oysters, mingle with fellow oyster enthusiasts, and support a great community organization. […]