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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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  • Maryland Folk Festival

    Make your plans now to join us in Salisbury, Maryland, for the Maryland Folk Festival— a diverse celebration of arts, culture, and heritage. This large-scale multi-day outdoor event, celebrates the […]

    Free

  • Chesapeake Film Festival

    Save the dates! The 2023 Chesapeake Film Festival (CFF) will be LIVE Sept. 30 and Oct. 1 at two historic venues in Easton, MD. The Festival goes VIRTUAL October 2 […]

  • Mid-Atlantic Small Craft Festival

    Hundreds of amateur and professional boat builders, model boat builders and enthusiasts come from all over the region to display their skiffs, kayaks and canoes. Watch many of these one-of-a-kind […]

    Free

  • Easton’s Fall Kickoff 2023

    Autumnal decorations and the feeling of seasonal warmth will be all around downtown Easton for a two day Fall celebration! Fall Kick Off /October First Friday Gallery Walk Giant pumpkins will […]

  • Easton Fall Craft Fair 2023

    OCT. 7, 2023 -- The second annual Easton Fall Craft Fair will take place from 10am to 3pm on Saturday, Oct. 7 at Trinity Cathedral, 315 Goldsborough St. in downtown Easton.   The indoor-outdoor fair is free and will feature 35 artisans selling one-of-a-kind crafts, from jewelry and pottery to seaglass art, crocheted toys, embroidery, […]

  • 8th Annual Easton Beer Fest

    Easton Volunteer Fire Department Ea315 Leonard Rieck Drive, Easton, MD, 21601, Easton, MD, United States

    SUPPORT LOCAL - DRINK LOCAL The 8th Annual Craft Beer Fest will be held on Saturday, October 7, 2023 from Noon to 4pm (VIP’s Enter at 11am). Maryland’s largest under cover craft beer festival will feature 40+ Breweries, Wineries and Distilleries will be pouring 120+ Craft Beers, Ciders, Seltzers, Wines & Spirits from the Mid-Atlantic […]

    $50

  • Oktoberfest in Berlin

    Berlin Oktoberfest & Sidewalk Sale 2 Bands! Authentic Oktoberfest music featuring The Edelweiss Band! Plus local favorite The Dunehounds perform sponsored by The Sterling Tavern Cascading Carlos Juggling Shows – Scales n Tales Animal Show Plus the Fall Sidewalk Sale! MORE Beer stations this year and featuring a variety of OCTOBERFEST beer too! German food featuring […]

  • Talbot County Fall Harvest Fair

    Talbot Agricultural Center 10659 Hiners Lane, Easton, MD, United States

    🌾 2023 Fall Harvest Fair - Celebrate the Season with Us! 🌾 Join us for a day of wholesome fun and community spirit at the Fall Harvest Fair on Sunday, October 15th, located at 10659 Hiners Lane, Easton, MD 21601. This event promises a fantastic time for families, friends, and all who cherish the joys of autumn. […]

  • Cruise-In at the Harvest Festival

    Talbot Agricultural Center 10659 Hiners Lane, Easton, MD, United States

    Come see the classics after the parade at the Talbot county Fall Fest   Cruise in from 12pm to 2pm

  • Tilghman Island Day 2023

    On Saturday, October 21st, 2023, from 10:00 a.m. until 7:00 p.m. the Tilghman Island Volunteer Fire Company will hold its annual Tilghman Island Day Celebration. A crowd favorite, the workboat-docking […]

  • Schellville’s Fall Fest in Rehoboth

    Tanger Outlets Seaside 36470 Seaside Outlet Drive Rehoboth Beach, DE 19971, Rehoboth Beach, DE, United States

    The folks that brought you Schellville's holiday extravaganza are getting ready for a fun fall fest. Indulge in a delightful culinary journey featuring the finest food trucks with scrumptious treats, […]

    $10

  • Sea Witch Festival in Rehoboth

    Rehoboth Avenue 509 Rehoboth Beach, DE,19971, Rehoboth Beach, DE, United States

    About the Sea Witch® Festival The annual Sea Witch Festival is Rehoboth Beach’s free family-friendly Halloween celebration. Dress up and enjoy the parades, live entertainment, contests and more in downtown Rehoboth Beach. The Sea Witch Festival is Friday through Sunday, Oct. 27-29, 2023. Sea Witch Festival Activities All through downtown Rehoboth, and at local businesses, […]