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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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  • 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.

  • Ice and Oyster Festival of Cambridge

    SCHEDULE CHANGE: Saturday, January 13th Noon-8 pm Join us for a day of Interacting with Amazing Ice Sculptures, Eating Oysters, Live Music, and Lots of Free Family Fun AT THE EVENT     See dazzling ice sculptures showcasing Eastern Shore culture, wildlife & more! Entertain your family with kid-friendly golf, thrones, ice slide, and other […]

  • Pirate & Mermaid Valentine Brunch

    About this event 2 hours Mobile eTicket $15-20 per ticket What better way to celebrate Valentine's weekend than spending it with the little ones that you love. Join us for […]

  • Endless Vision’s Valentines Gala

    About this event 5 hours 30 minutes Mobile eTicket $50-75 per ticket come out and enjoy yourselves with some live music good vides with a prom theme and setting with […]

  • 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 […]

  • Chesapeake Fire & Ice of Easton

    Chesapeake Fire & Ice Festival Returns to Easton, MD in 2024! Larger-than-life sculptures made of solid ice will be on display throughout the historic downtown! Festival will feature dozens of […]

  • 6th Annual St. Michaels ChocolateFest

    Town of St. Michaels 101 N Harbor Rd, St.Michaels, MD, United States

    St. Michaels ChocolateFest will be held March 2, 2024 and will include restaurant chefs conjuring up amazing delectable special menu items to showcase chocolate inspired dishes and desserts.  The Chocolate Crawl […]

  • 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, […]

  • St. Patrick’s Day Celebration Dinner in Oxford

    Oxford Community Center 200 Oxford Road, Oxford, MD, United States

    Traditional Irish dinner: MARCH 14 @ 6:00 PM Corn beef, Cabbage, Potatoes and Irish Soda bread (prepared by a team of OCC chefs) $25/person (with cash bar) Live Music  Reservations by March […]

    $25

  • Opening day at Scottish Highland Creamery

    Opening day at Scottish Highland Creamery from 3:00 pm to 8:00 pm. Face painting 3:00 – 5:00, new ice cream flavors, special prize for 1st customer of the season! DETAILS […]