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.

  • 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 the patio with some of the best Pinots! Join us for dinner at $100 per person or Saturday tasting at $50. We welcome our beloved […]

  • 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 make sure to come join the coolest IMMD ride in the land! My team and I are organizing a group ride of the IMMD bike […]

  • 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. […]

  • Emily’s Produce Sunset In The Stalks in Cambridge

    Who's ready to kick this fall season off with a bang?? WE ARE!! Because we just can't wait any longer, we are opening the maze a whole week early for ONE EVENING ONLY (and for special summer admission pricing too)! We'll have Good Times Entertainment here bringing the happy tunes, lots of fun snacks & […]

  • 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 […]

  • 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

  • 57th Annual Maryland Seafood Festival in Annapolis

    Maryland Seafood Festival is back with another year of tasty tradition! Saturday AND Sunday 11am-7pmFeaturing live music performances, chef demonstrations, delicious seafood, creative craft booths, and an interactive kids zone - it's guaranteed to be a shell of a good time! Event by Maryland Seafood Festival Venue: Sandy Point State Park East Beach Duration: 2 […]

  • Light Night celebrating the Choptank River Lighthouse in Cambridge

    Light Night is a celebration of the Choptank River Lighthouse and all that it means to Cambridge and Dorchester County! The annual LIGHT NIGHT will be held Saturday, September 14, 2024 at the Cambridge Yacht Club. A celebration of the Choptank River Lighthouse and the difference “The Jewel of the Choptank” is making for our […]

  • September’s Beer and Brushes at Ten Eyck Brewing in Queenstown

    September's Beer and Brushes at Ten Eyck Brewing is open for registration! We'll be painting "Shorebird" and you'll receive a token for your first drink. Try a new beer or grab an old favorite and the field kitchen will be available for purchasing great eats for the evening. We'll walk you through each element- you […]