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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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Talbot County

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  • Wine Tasting at St. Michaels Winery

    Wine tastings Hours Monday - Saturday (12pm-5pm) Sunday (12pm-4pm)  With 18 wines in our cellar, we have something for every pallet. Tasting Fee: $1.00 per wine sampled Glasses:  Glasses of […]

    $1

  • St. Michaels Farmer’s Market

    The St. Michaels Farmers Market features farmers and vendors selling locally grown and caught vegetables, meats, and fish, plus handmade crafts and live music.The St. Michaels Farmers Market features farmers […]

    Free

  • Classic Motor Museum Memorial Day Parade

    The CMM is proud to bring our community together in honoring the service of our military heroes by hosting the Annual Classic Motor Museum Parade. The participants will line up […]

    Free

  • St. Michaels Yacht Beer Tasting Cruise

    Available per person or Private Charter Join us for an unforgettable experience on our ice-cold Beer Tasting Cruises Be prepared for an unforgettable adventure on our beloved historic yacht Sail […]

    $115

  • St. Michaels Yacht Wine Tasting Cruise

    Enjoy a truly unforgettable wine tasting experience on the Chesapeake Bay with Sail Selina II. Our 2-hour St Michaels, MD wine tasting cruises are the perfect way to indulge in […]

    $115

  • Chesapeake Bay Champagne Sunset Sail

    Looking to go sailing at sunset while sipping champagne? This is the sunset champagne charter for you! Come join us for a relaxing 2 hour cruise near Annapolis. Your St […]

    $115

  • Easton Farmers Market

    From local produce growers to watermen, from bakers to crafters and local artisans, the Easton Farmers Market provides an entire meal, home décor and unique gift items in a friendly […]

    Free

  • St. Michaels Brewfest 2023

    On June 3rd, from 12:00 pm - 4:00 pm come out to the St. Michaels Brewfest 2023! They offer Three Pouring Venues, Over A Dozen Breweries, Art, Glassware, Food, and […]

    $55 – $110

  • Delmarva Pride Festival

    Delmarva Pride 2023 Delmarva Pride takes place over the weekend 16th to 18th June 2023.

  • Delmarva Pride Presents 2nd Annual Drag Show

    If you attended last year’s event, you know this show is going to be a wonderful night of entertainment fit for a queen! As part of its Annual Pride Weekend, […]

    $20 – $30

  • St. Michaels Ghost Walk – Spirits of Rowdy Women

    The walk begins in front of the Chesapeake Bay Maritime Museum and makes its way through around the St. Michaels harbor and around St. Michaels historic downtown. Visit an old […]

    $25