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.

  • 20th Annual Eagle Festival

    The 20th Annual Eagle Festival at Blackwater National Wildlife Refuge on Saturday, March 16, 2024, from 9:00 a.m. to 4:00 p.m. as we celebrate birds of prey! Don’t miss out […]

  • Cambridge Rotary Community Foundation Oyster Festival

    Join us for a shuckin' good time at the Cambridge Rotary Community Foundation Oyster Roast! Indulge in delicious oysters, mingle with fellow oyster enthusiasts, and support a great community organization. […]

  • Adult Easter Egg Hunt 2024

    Join in the fun at Layton's Chance! This adult only Easter Egg hunt is a twist on the traditional hunt! At 6:00pm blindfolded teams of 2 will compete during fun […]

  • The Eastern Shore Sea Glass and Coastal Arts Festival

    The Eastern Shore Sea Glass and Coastal Arts Festival brings artisans and craftspeople who will exhibit and sell coastal and sea-glass related jewelry, home décor, art, and more. The popular festival runs 10am–5pm Saturday and 10am–4pm Sunday, with all tickets valid for admission on both days. Each ticket includes entrance to the Eastern Shore Sea […]

  • Cambridge Craft Market and Food Drive

    Blue Ruin is teaming up with One Mission Cambridge to host the Cambridge Craft Market and Food Drive! From 3pm to 9pm on Friday, April 26th, visit Blue Ruin’s parking […]

  • 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