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.

  • 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. • Don't forget to stop at the Choptank River Lighthouse while there! August 31 3-5 PM Cambridge, Maryland Day Sail Adults $55 12 and Under […]

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

  • 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 WEEK: Event by Kent Island Farmers' Market Kent Island Farmers' Market OUR USUAL VENDORS:Dimitri Olive OIl: Olives, Olive oil, Infused Olive oil & Balsamics, Tapenades, […]

  • 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 […]

  • Councell Farms Opening Day near Easton

    Councell Farms Opening Day! Come visit the Field of Fun, market and get our farm fresh ice cream! Open daily 9:30-5:30 until October 30th. Event by Councell Farms Venue: 11773 […]

  • 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 […]

  • 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 […]

  • Annual End of Summer Crab, Bull, and Oyster Roast In Grasonville

    Join us for our annual End of Summer Crab, Bull, and Oyster Roast! Enjoy crabs, oysters, pit beef, pulled pork, corn on the cob, coleslaw, domestic beer, wine, and seltzers, along with live music! Don't miss out, as this event sells out every time Event by Jetty Dock Bar 201 Wells Cove Rd, Grasonville, MD, […]