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.

  • Academy Art Museum in Easton

    WHERE ART IS FOR EVERYONE Welcome to the Academy Art Museum! Plan your visit with us and discover something new. OPEN TODAY 10:00 AM  - 7:00 PM | FREE ADMISSION EVERY […]

  • Tiger Lily Restaurant & Tiki Bar & More Summer Events

    the KG Band will be rockin' Tiger Lily again. Come dance and listen to some of your favorite Classic Rock tunes while you enjoy the awesome Tiger Lily Tiki Bar. […]

  • Talbot County Fair Celebrating 40 Years in Easton

    The Talbot County Fair is held every year during the second week in July. It is open to the public. Lots of Fun, Food, Entertainment and More!! For more information, […]

  • Ironman Course Group Ride in Cambridge

    Event by Tim Delss Cambridge-South Dorchester High School Come out and join us for a group ride of the IMMD bike course! That's right, we're back for another year so […]

  • Clipper ship Pride of Baltimore II In Cambridge

    Head to Cambridge, Md. Labor Day weekend to see the glorious replica clipper ship Pride of Baltimore II. Dock tours, day sails, sunset sails, Aug. 31 to Sept. 2. Details. […]

  • Skipjack Race & Festival

    Festival Grounds includes Food Vendors, Arts & Crafts Vendors, Heritage & Education Exhibits and free Children's Activities, both Sunday and Monday The Deal Island (Md.) Skipjack Races happen on Labor […]

  • Labor Day Parade in Grasonville

    Event by Grasonville Community Center Grasonville Community Center Monday September 2nd 5601 Main Street, Grasonville MD Parade starts at 12pmLine up starts at 10am Following the parade there will be […]

  • Kent Island Farmers Market Fall Opening

    Kent Island Farmers market is in their winter hours 3:30-6:00We are a year round farmers market! All vendors accept credit cards and or online payments POP UP VENDORS FOR THIS […]

  • Emily’s Produce Harvest Celebration in Cambridge

    Who's ready for Fall on the farm?? WE ARE!! Come kick start your Fall season with us at our Harvest Celebration-it's the OFFICIAL start of Autumn at Emily's and the […]

  • Rockfish Rodeo Fishing Tournament and Crab Feast in Grasonville

    2024 Rockfish Rodeo Fishing Tournament and Crab Feast Benefitting Talisman Therapeutic RidingSeptember 9, 2024All Boats Launch from Fisherman's Crab Deck at 6:00 AM Sign Up Now:Sponsorships Available!Single Anglers - $225 […]