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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 chat with our enthusiastic staff - We Love All Things Italian!  We also offer free tastings all week long.  Salute!

  • 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, […]

  • 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, […]

  • 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 […]

  • Mother’s Day Weekend Stop and Shop in Easton

    Come and shop all things! Free beverage and mini bouquet for all registered guests. Register here: https://www.surveymonkey.com/r/H7N3BXC Vendors: Lemon and Sage Boutique Get on Board A&M Heirloom Rentals Fruitful Clay […]

  • Mimosas for Mommy in St. Michaels

    Celebrate Mom in Style at The Galley Restaurant! Treat Mom to an unforgettable Mother's Day experience at our 4th Annual Mimosas for Mommy Celebration! Indulge in a relaxing brunch that […]

  • Waterfront Concerts in the Park Kick Off in St. Michaels

    The St. Michaels Community Center is pleased to announce our 2024 schedule for our Concerts in the Park series, kicking off on Thursday, May 30, 2024 and continuing every Thursday […]

  • St. Michaels Brew Festival

    St. Michaels Brewfest is celebrating 10 years! Brewfest continues to bring specially crafted regional and National beers to this Pre Summertime Beer Festival! Offering the full spectrum of beers from […]