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.

  • 10th Annual Sudlersville Peach Festival At Godfrey’s Farm

    Organizer: Event by Godfrey's Farm and Sudlersville Volunteer Fire Company Venue: Godfrey's Farm 302 Leager Rd, Sudlersville, MD 21668-1310, United States Date: August 2nd from 6pm to 9:30pm August 3rd from 10am- 4pm Local bands providing live music, community non-profit groups serving great homemade food from pit beef to peach cobbler, local vendors offering their […]

  • Queen Anne’s County Fair in Centreville

    View the website below for all this fair offers! Organizer: Event by Queen Anne's County 4-H Fair Venue: Centreville, MD, United States, Maryland 21617 Website: https://www.qacfair.com

  • The Crab Feast in Easton

    Join us for an evening of delicious crab dishes, refreshing drinks, and great company! Don't miss out on the fun - get your tickets now! Event by Helen and Rae’s […]

  • Pinot on the Patio in St. Michaels

    Join us for a weekend of everything Pinot! Friday night - a multi-course dinner by Stephanie Cook, chef and owner of Wonderment Wines. Saturday - enjoy an afternoon tasting on […]

  • 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 Day Monday, Sept. 2. As always, the Island Fest on both Sunday and Monday offers a variety of events—parade, live music, car show, blessing of […]

  • 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 vendors, food, moon bounce, music, 50/50 raffle & lots of fun!

  • 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 opening weekend of our 2024 corn maze!! We'll be opening the pumpkin patch & the corn maze, we'll have so many yummy fall treats (apple […]

  • 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 (Includes Crab Feast)Single Crab Feast Guest - $110 Event by Talisman Therapeutic Riding Venue: Fisherman's Crab Deck Tickets: https://talismantherapeuticriding.networkforgood.com/events/72262-2024-rockfish-rodeo-crab-feast?fbclid=IwY2xjawE6yX9leHRuA2FlbQIxMAABHZLDkTYwkaLLXokhMitgC4U6Pc3yRJXxjuQKaTOgK4vdjlDxxZjpXelFsw_aem_XNEsl_IrlSysCAuQJHzpoA