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.

  • 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 […]

  • 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 […]

  • 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 […]

  • Blooms and Brews @ Corah’s Corner and more Summer Events

    Join us for a fun blooms and brew experience. Arrange beautiful local flowers while tasting local brews on Corah’s beautiful deck! NOTE: This event is July 19. Tickets: https://l.facebook.com/l.php?u=https%3A%2F%2Fwww.vintagefamilyfarms.com%2Factivities%3Ffbclid%3DIwZXh0bgNhZW0CMTAAAR29aRbzkisG7updQs8W6QwoQUuiDjQtpqsZEgMuzZwBNf_BUk6WixpR4Sg_aem_jaPb6rlFwyuLZL6_3EYVYA&h=AT2LZZbtn1QPXSHUoCX1GnfTdX1ulC0dUqQ-z3FEkpUZHwcqG55dXfEE_BfCoc-V059f-1Nx9ja7YURUXB57yPQXZsvb3yx7HUieILJB8-fI7R8sY9MFm1Ob2OaNq2vTUrKexIJxiATtQRTv2I74DUJ-3GI Event […]

  • 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, Check out the website at www.talbotcountyfair.org Venue: 10659 Hiners Ln, Easton, MD, United States, Maryland Organizer: [email protected]

  • 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 […]

  • 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!

  • 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, […]