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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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St Michaels

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  • 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 […]

  • 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 […]

  • Annual Multicultural Festival in Easton

    Save the date! The Avalon Foundation’s Annual Multicultural Festival returns to Easton’s Idlewild Park with a fun day of diverse musical traditions, arts, and food on Saturday, May 4, 2024, […]

  • Spring Paint & Sip

    Spring is in the air, and brighter days are ahead. Looking for a fun excuse to get out of the house? Well, look no further. Far Eastern Shore Winery will […]

  • Kent Narrows Boat Expo

    3 Weekends to browse, tour and shop new and used boats.   The docks are connected from Safe Harbor Narrows South to Fisherman's Village with access to docks at Crab […]

  • Tequila and Tulips

    Vintage Family Farms and Corah's Corner are teaming up again to bring you a create your own Tulip bouquet bar with our own field grown Tulips and your favorite Tequila […]

  • The Eastern Shore Sea Glass and Coastal Arts Festival

    The Eastern Shore Sea Glass and Coastal Arts Festival brings artisans and craftspeople who will exhibit and sell coastal and sea-glass related jewelry, home décor, art, and more. The popular […]

  • VIP WineFest 2024

    Old Brick Inn Properties 401 S. Talbot, St. Michaels, MD, United States

    VIP WineFest 2024 We are pleased to announce WineFest 2024! We are bringing back WineFest 2024. Wine will be tasted from many countries around the world! Wine will be poured, […]

  • St. Michaels Wine Tasting Crawl

    Uniquely arrive in charming St. Michaels, Maryland by boat! Depart from @kentmorrmarina and enjoy light appetizers with beautiful views to St. Michaels harbor, enjoy the Wine tasting crawl and re […]

  • Jazz on the Miles River in Saint Michaels

    Sip cocktails and enjoy the sounds of JG and the Initials aboard PATRIOT while floating on the gentle waters of the Miles River on a 90-minute cruise. In the early […]

  • JCT 33 on the Patio at Corah’s Corner

    Join us on Saturday, May 4th for JCT 33 on the patio! 6-9pm Live & Local! Let’s kick off our Music Season the proper way! Come JOIN us for some […]