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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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Today

  • 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 […]

  • IRONMAN 70.3 Eagleman

    Gerry Boyle Parl Somerset Ave, Cambridge, MD, United States

    Take Flight and Soar An authentic Chesapeake town on Maryland’s storied Eastern Shore, lies the historic IRONMAN 70.3 Eagleman. A big race for a small town, experience Cambridge’s history and charm […]

  • Sip | Savor | Shop in Easton

    Sip | Savor | Shop invites you to join us for an evening of culinary delights and shared moments. At the event, you can sample our Greek gourmet products, including […]

  • Dancing Under the Stars in Snow Hill

    Dance the night away with music by Classic Vibe. FREE to attend. Food and fun! Cash Bar with all proceeds going to Downtown Snow Hill, Inc. Venue: Event by Downtown […]

  • Old School R&B Crab & Cruise in Crisfield

    Get ready for the ultimate seafood extravaganza of the summer! This event has premium crabs measuring 6 1/4" up to 8"! 97.5FM DJ, Big Mark will be mixing up the R&B/Hip Hop hits from 90's and 00's on the upper level of the cruise while music plays on the lower level. Hurricane Hazel will be […]

  • Adult Field Day at the Layton’s Chance Winery in Cambridge

    Step back into the carefree days of childhood with a twist at our Adult Field Day at the Winery. This event promises a delightful blend of nostalgia, fun, and friendly competition. Get ready to unleash your inner child with a series of classic field day games, all with an adult-friendly spin. Wear your favorite retro […]

  • The Famous Annapolis City fireworks from the Water

    Come celebrate your Independence with us. Enjoy the famous Annapolis City fireworks from the water! Public 3 hour cruise includes a tour around the harbor, sunset, and then front row seats to the see fireworks! Memories are sure to be made. Book Today: www.TourBoatAnnapolis.com (443)333-1030 Event by Tour Boat Annapolis Venue: Annapolis, MD

  • Live Music all Summer at Foxy’s Harbor Grille in St. Michaels

    Event by Foxy's Harbor Grille Venue: 125 Mulberry St, Saint Michaels, MD, United States, Maryland 21663 TODAY Groove Tide 5-8pm FRIDAY Uncle Ward 5-8pm SATURDAY Mike Miller 4-7pm SUNDAY Brandon & Thordis 4-7pm Be sure to check out our Events Tab on Foxy’s Facebook to see our Live Music Schedule for the summer! 🎶☀️ https://www.facebook.com/FoxysHarborGrille/events

  • Easton’s 4th of July Celebration Carnival

    Family Fun Carnival! On July 4th the Carnival will be open from 4-11pm and as soon as it gets dark the fireworks will light up the sky! Wristbands offered nightly!!! Excluding the 4th Event by Shaw and Sons Amusements Venue:Grounds behind Target, 28539 Marlboro Avenue, Easton.