Want a fun, relaxing getaway this summer? Plan a trip to a small town on the Eastern Shore to align with these festivals and other events happening soon.
Chestertown Tea Party Festival
May 26–28
As legend has it, Chestertown residents tossed the cargo of a British ship overboard in 1774. At this festival, you can watch the reenactment of the Chestertown Tea Party. The Memorial Day weekend events include a block party, parade, raft race, live music, and a beer fest. Chestertown Historic District; Wilmer Park: 413 S. Cross St., Chestertown, Maryland, free
Plein Air Easton Art Festival
July 12–21
Celebrate the 20th anniversary of this outdoor juried competition. Watch plein air painters create masterpieces outdoors and paint for two hours yourself, with the chance to sell your work. Enjoy workshops and art galleries throughout the week. S. Harrison Street, Easton, Maryland, free, $10 for Quick Draw painting event
99th Annual Chincoteague Pony Swim and Auction
July 20–26
Catch the action as Saltwater Cowboys round up horses and foals on Assateague Island for the annual swim to Chincoteague, where they will be auctioned off the next day to raise money for the fire department. Hit the carnival grounds for rides and games for the kids, food, and live entertainment. Veterans Memorial Park: 7470 Memorial Park Dr.; Carnival Grounds: 3648 Main St., Chincoteague, Virginia, free
The Great Pocomoke Fair
August 8–11
The Bullride Mania Rodeo Company brings the rodeo to the fair. Check out rides, a demolition derby, antique tractor pulls, and harness racing. Plus, lots of carnival food. 2037 Broad St., Pocomoke City, Maryland
Rock Hall Pirates & Wenches Weekend
August 9–11
Set sail for a weekend filled with pirate-themed entertainment and activities in Rock Hall. Families can don their best buccaneer garb and join a sea shanty sing-along, while adults will get the chance to try rum at a tasting event. Main Street, Rock Hall, Maryland, free, $25 for rum tasting event
77th National Hard Crab Derby
August 30–September 1
Crisfield’s annual crab festival comes alive as the town races hundreds of crustaceans to celebrate the waterfront community that’s known as the Crab Capital of the World. There will be a crab parade and an array of seafood-oriented activities. The weekend features live entertainment, a 5K and a 10K race, and crab cooking and picking contests. Somers Cove Marina: 715 Broadway, Crisfield, Maryland, free
Wine on the Beach
September 6–7
Indulge in Maryland’s finest wines at Ocean City’s inlet. You can catch some performances by bands and shop from vendors offering clothing, gifts, and food. Ocean City Inlet, Maryland, $35; $15 for ages 13 to 20; free for ages 12 and under
Annual Dorchester Center for the Arts Showcase Event
September 29
This annual art street festival is a family-friendly event that spotlights the creativity of Delmarva artists. Stroll through Cambridge to see the mix of artworks, from paintings to ceramics. High Street, Cambridge, Maryland, free
51st Annual Chincoteague Oyster Festival
October 12
Feast at this seafood festival where oyster dishes reign supreme. Enjoy clam chowder, shrimp cocktail, raw and steamed oysters, clam fritters, and more. Festival favorite Island Boy will provide live music. Tickets must be purchased in advance. Tom’s Cove Park: 8128 Beebe Rd., Chincoteague, Virginia, $65, free for ages 5 and under
Editor’s note: This post has been updated to remove events that occurred earlier in May.
Feature image by de Art/stock.adobe.com
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This story originally ran in our May issue. For more stories like this, subscribe to Northern Virginia Magazine.
