A Cinderella of the Chesapeake, this Eastern Shore gem has transformed itself into a lively beach town with great seafood and charming historic homes. Follow our itinerary for a dreamy weekend trip.
By: Marisa Spyker
1 of 7Photo: Chris M. Rogers
Friday / 5 P.M.
Start the weekend with a wine tasting at Gull Hummock Gourmet Market, a wine, beer, and specialty foods shop in the heart of downtown. Pick up some Seaside Gourmet Chocolate (757-331-1500) while you’re there.
Pictured: Chilling at Gull Hummock Gourmet Market
2 of 7Photo: Chris M. Rogers
Friday / 7:30 P.M.
Saunter to The Shanty, where the party continues on the open-air deck, with cold beers, cornhole, and fresh seafood (try the fried oyster po’ boy with lemon-caper aïoli).
Pictured: Soft-shell crab, oysters, and crab-topped burger at The Shanty
3 of 7Photo: Chris M. Rogers
Saturday / 10 A.M.
Stroll downtown’s historic district with its late 19th- and early 20th-century architecture. Key stops: Moonrise Jewelry, Meredith Restein’s gallery of coastal pieces; At Altitude Gallery, which showcases Gordon Campbell’s breathtaking aerial photography; and Brown Dog Ice Cream, an elevated scoop shop that’s open seasonally. (You can pick up pints at Gull Hummock year-round.)
Pictured: Sweet stuff at Brown Dog Ice Cream
4 of 7Photo: Chris M. Rogers
Saturday / 2 P.M.
Count your blessings: This is a town that doesn’t make you choose between active hour and happy hour. The Paddle Your Glass Offguided kayak tour with SouthEast Expeditionstakes you on a 45-minute paddle along the marshy banks of Church Creek (a birding mecca) and then drops you on the shores of Chatham Vineyardsfor a wine tasting (just keep in mind you’re paddling back!).
Pictured: Feeling the love every day in Cape Charles
5 of 7Photo: Chris M. Rogers
Saturday / 5 P.M.
Catch a Chesapeake sunset while dining on fresh-from-the-bay seafood like local oysters, clams, or Maryland blue crab cakes at the just- upscale-enough- for-Saturday-night Oyster Farm Seafood Eatery at Kings Creek.
Pictured: Dockside at Oyster Farm Seafood Eatery
6 of 7Photo: Chris M. Rogers
Sunday / 9 A.M.
Do up brunch (or just linger over coffee) at the two-story, Art Deco–style Cape Charles Coffee House, a beloved-by-locals spot.
Pictured: Taking it easy like Sunday morning at Cape Charles Coffee House
7 of 7Photo: Chris M. Rogers
Sunday / 11 A.M.
Cap off the weekend with a round at Bay Creek, an award-winning golf resort that features signature courses, each with prime water views, from both Jack Nicklaus and Arnold Palmer. Your post-round beer awaits at Coach House Tavern.
Pictured: Seeing double over Palmer Lake as the sun sinks below the horizon