Eastern Shore of Virginia and Maryland Events May 2018

Festivals, parades and celebrations on the Eastern Shore of Virginia and Maryland's Eastern Shore in May of 2018.


May 4, 2018 - Chestertown First Fridays. Shops and restaurants in downtown Chestertown stay open late and host special events. Chestertown, MD.

May 5, 2018 - Six Pillars Centrury Bike Ride. This cycling event at Blackwater National Wildlife Refuge has three courses to choose from. Cambride, MD.

May 5, 2018 - Chincoteague Seafood Festival. All-you-can-eat seafood feast, plus live music. Held at Tom's Cove Park on Chincoteague Island. Noon to 4:00 p.m. Chincoteague, VA.

May 12, 2018 - Somerset Strawberry Festival. Strawberries, live music, exhibits, kids' activities, and more. Held in Marion Station, MD.

May 12, 2018 - Second Saturday in Cambridge. Shops and galleries stay open late with specials, art gallery receptions, and more. Cambridge, MD.

May 19, 2018 - St. Michaels Running Festival. Multiple foot races, including a half marathon. St. Michaels, MD.

May 19, 2018 - Kent Island Day. This event commemorates the 1631 founding of Kent Island with a parade, historic exhibits, and more. Kent Island, MD.

May 20, 2018 - Community Day & Maritime Model Expo at Chesapeake Bay Maritime Museum. Free admission, live music, regional food & drink, family activies, and boat rides, plus model boat exhibits, demonstrations, and races. St. Michaels, MD.

May 25 - 27, 2018 - Chestertown Tea Party. Big annual weekend event marking Chestown's Colonial rebellion against the tea tax. Wide variety of events scheduled. Chesertwon, MD.

May 27, 2018 - Soft Shell Spring Fair. Annual festival with seafood, live entertainment, and arts & crafts. Crisfield, MD.