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.

Looking for events near your rental? Browse vacation rentals by town.

  • Coastal Crab Art in Cambridge

    Event by Prodigal Creations Of Princess Anne   Venue: 1000 goodwill ave Cambridge Md   Tickets: https://l.facebook.com/l.php?u=https%3A%2F%2Fsquare.link%2Fu%2FfErOwYqZ%3Ffbclid%3DIwZXh0bgNhZW0CMTAAAR0KbCjOiy2Aa42_hIhL3dOfi4Ph4WHnAT8hWN2BpgDUHAyVbeinGzFyLxA_aem_AdUE1ZDJadUPgWXmDf4nZ8-3qPkAa3jAx5yj79L_4jq5VB9meuy0eCDjqzdxWb_Jv888iL_eklZln32zm3Qi4Wqq&h=AT0rSgshAHtpyMe4RIfBDkY0VNO8Cmu7sUSTXQdUSY-XFPtnEOLWDsopCCjSiCy7I3CPcWaSELMhkj0OzUySVKM0XZX2Zx9oGQu_ZesJC6F7SkF2IjjNra_AHD8OjuQ15gALFEC8OfsTNzf78FSvkQiWMWE

  • 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 […]

  • Chamber Music Festival 2024

    Ebenezer Theater 17 S Washington St, Easton, MD, United States

    More information coming soon!

  • 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 while enjoying the vibrant art scene, local restaurants and breweries, fresh seafood, and family-friendly adventures. With over 25 years of racing, get ready to soar towards the finish […]

  • 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 a red and white wine, artisanal hard and soft cheeses, filo-wrapped delights like spanakopita and tiropita, a variety of Greek olives, and some of the […]

  • 36th Annual Antique and Classic Boat Festival and Costal Arts Fair in St. Michaels

    We cannot wait for the 36th Annual Antique and Classic Boat show at the Chesapeake Maritime Museum in beautiful Saint Michael’s, Maryland. This year, the theme is “It’s All About Fishing”. Come see amazing antique boats, classy classic boats, and awesome vendors! Registration for vendors and boats is open now! Venue: Chesapeake Bay Maritime Museum […]

  • Easton’s Farmers Market

    The Easton Maryland Farmers Market has been operating for over 40 years. Located in the municipal parking lot in the 100 block of North Harrison Street the pedestrian-only market features live music every Saturday at 10:30. All of our vendors are cultivating, producing, cooking and crafting their inventories so be sure to stop by and […]

  • 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 Snow Hill in Sturgis Park Organizer: Sturgis Park

  • Easton Trivia Nights at Doc’s Downtown Grille

    Let's Do Trivia! is a weekly, team-based, live-hosted pub and restaurant trivia game show. FRIENDS * FOOD * FUN! FREE TO PLAY - BIG PRIZES TO WIN! $40 First Place + more! Our team-based trivia game is perfect for groups of friends, family, or co-workers. Let's Do Trivia! gives you time to answer questions while […]

  • 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 […]