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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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  • 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 […]

  • 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 a fun morning filled with great food, fun crafts, family-friendly games, and more. Date and time Saturday, February 10 · 11am - 1pm EST Location […]

  • 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 a red carpet that meets you to your car with a photographer waiting to flick you up as well as proformances by Ms Ayla Dennis […]

  • 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 […]

  • 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 ice sculptures throughout Easton’s Historic District. Friday nights kick off will feature live ice carvings, music, and restaurant specials. The celebration will offer free live […]

  • 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 […]

  • 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 […]

  • 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 […]

  • 2nd Annual Peake Irish Experience for Annapolis St Patrick’s Day

    About this Event Get ready for our second St. Patrick's Day bar celebration with authentic Irish beverages for the biggest Irish holiday! Introducing The Peake Irish Experience, an Irish bar journey brought to you by Peake Social, Guinness, Emerald Society of Firefighters, and in partnership with Shamrock the Dock! Join us as we make our […]

  • 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 […]