You are here: / / Dorchester County

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.

Dorchester County

Events

Events Search and Views Navigation

Event Views Navigation

Today

  • Cambridge Traditional Crab Run

    We are excited to say that we are returning for our traditional Sunday (Mother's Day) event!!! The Crab Run consists of a half marathon (13.1 miles) immediately followed by a […]

  • 2024 Cambridge Classic Powerboat Regatta

    Racing since 1911, the oldest active powerboat race in the country happens right here in Dorchester County, Maryland. This year's race will be held on May 18-19, 2024 on the […]

  • Coastal Crab Art in Cambridge

    Event by Prodigal Creations Of Princess Anne   Venue: 1000 goodwill ave Cambridge Md   Tickets: https://l.facebook.com/l.php?u=https%3A%2F%2Fsquare.link%2Fu%2FfErOwYqZ%3Ffbclid%3DIwZXh0bgNhZW0CMTAAAR0KbCjOiy2Aa42_hIhL3dOfi4Ph4WHnAT8hWN2BpgDUHAyVbeinGzFyLxA_aem_AdUE1ZDJadUPgWXmDf4nZ8-3qPkAa3jAx5yj79L_4jq5VB9meuy0eCDjqzdxWb_Jv888iL_eklZln32zm3Qi4Wqq&h=AT0rSgshAHtpyMe4RIfBDkY0VNO8Cmu7sUSTXQdUSY-XFPtnEOLWDsopCCjSiCy7I3CPcWaSELMhkj0OzUySVKM0XZX2Zx9oGQu_ZesJC6F7SkF2IjjNra_AHD8OjuQ15gALFEC8OfsTNzf78FSvkQiWMWE

  • 17th annual St. Michaels Concours d’Elegance on Chesapeake Bay & 8th Annual Chesapeake Bay Motoring Festival

    Kent Island Yacht Club will host two prestigious events this year – the 8th annual Chesapeake Bay Motoring Festival on June 8-9, and the 17th annual St. Michaels Concours d’Elegance on Chesapeake Bay on September 27-29. Both events are presented by St. Michaels Concours d’Elegance on Chesapeake Bay. Venue: Kent Island Yacht Club The event […]

  • 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 R&B/Hip Hop hits from 90's and 00's on the upper level of the cruise while music plays on the lower level. Hurricane Hazel will be […]

  • Adult Field Day at the Layton’s Chance Winery in Cambridge

    Step back into the carefree days of childhood with a twist at our Adult Field Day at the Winery. This event promises a delightful blend of nostalgia, fun, and friendly competition. Get ready to unleash your inner child with a series of classic field day games, all with an adult-friendly spin. Wear your favorite retro […]

  • Wine & Design Wine Bottle Bird Feeder at Layton’s Chance in Cambridge

    Each guest will sand and stain or paint their own bird feeder. Choose your recycled Layton's Chance wine bottle and fill with bird seed before you go! Your feeder will be ready to hang when you leave. *DIY construction kits are also available Tickets: https://lp.constantcontactpages.com/ev/reg/deyws5z?fbclid=IwZXh0bgNhZW0CMTAAAR1Jc37b03FOtZR_qjtG5K6brKHF6Ai7L4nDIEgq-Q2f6VyUNlV63xFbem0_aem_AdmWSRPOrHfzIy0ylJzcCx47Zfi6RhR8gBOs9pZwVT3c_KUdAuOJBXeL09393JKgHluvhtdyEv88FC3az22YkRdV Organizer: Event by Layton's Chance Vineyard & Winery Venue: Layton's […]

  • 4th of July Fireworks in Cambridge

    The City of Cambridge will have their Annual 4th of July Fireworks Firework display beginning at Dusk from Gerry Boyle Park at Great Marsh over the Choptank River. Date and […]

  • 2024 Breaker Rock Beach in Cambridge

    Faith Baptist Fellowship and Cambridge Wesleyan Church present our 2024 Vacation Bible School... Breaker Rock Beach-Gods rock solid truth in a world of shifting sands. Romans 12:2. This VBS will […]

  • Snappers Waterfront Tiki Events this Summer in Cambridge

    Check out the website for Open mic nights & Live Music! http://www.snapperswaterfrontcafe.com/ 112 Commerce St, Cambridge, MD 21613 Monday: 11:00 AM - 8:00 PM Tuesday: 11:00 AM - 8:00 PM Wednesday: 11:00 AM - 8:00 PM […]

  • Thunder on the Choptank Boat Races in Cambridge

    When you hear the roar of automotive engines and catch a glimpse of giant roostertails, chances are pretty good that inboards are on the water. As the largest category in […]