1. Where to Stay
Enjoy loft-inspired living at the Cape Charles Blue (from $130), where six 700-square-foot suites feature exposed-brick walls dating back to 1900 and full kitchens built with reclaimed wood from the original structure. Housed in what was once a nickel and dime store, the hotel is a short walk from the beach, where you can watch the sun set over Chesapeake Bay.
Book one of the second-floor rooms with private glass-and-wood balconies that overlook the harbor at Hotel Cape Charles (from $170), opened last spring on the main thoroughfare of Mason Avenue. Though the building has served as a hotel for more than a century, its latest incarnation features contemporary touches like Carrara marble countertops and glass mosaic tiles along with comforts like handmade Cozy Pure mattresses and complimentary breakfasts.
Have oysters and wine on your own private beach at Eagle’s Rest Beach House (from $3,900/week), an airy, three-bedroom waterfront house located north of Cape Charles. Designed by New York architect Tom Hickey, the home sports floor-to-ceiling windows, gorgeous mosaics, and a luxe kitchen alongside an open dining room that seats up to ten people.
2. Where to Eat
See waves crashing from your table at the Island House Restaurant (open Thursday to Sunday in the winter) in the fishing village of Wachapreague, where chef Charles Thain serves up local seafood in a salt-marsh setting. Try Sewansecott oysters (often on the menu at Grand Central Oyster Bar) on the half shell ($8 for a half-dozen) or the signature Oysters Parramore with local crabmeat and a secret sauce ($14).
Slide into a hammock while waiting for a casual lunch at Woody’s Beach BBQ on Chincoteague Island, where you can choose between two menus: one packed with house-smoked meats and slow-cooked barbeque and the other with fresh seafood. Order a shrimp po’boy sandwich ($10.99) topped with crunchy slaw, or a slab of baby back ribs ($13.99 for a half-rack) along with sides like cornbread and sweet-potato fries.
Slurp freshly shucked oysters ($8 for a half-dozen) at the Shanty, which opened last summer on the harbor in Cape Charles. Under the pitched wooden roof, bright-blue walls showcase artistic photographs of local fishermen, live musicians play acoustic sets, and the kitchen turns out baskets of fried oysters ($14) and massive seafood platters ($23) with crab, oysters, fish, hush puppies, and corn on the cob.
3. What to Do
Board an oyster barge for a private two-hour tour ($35; book two weeks in advance) at Cherrystone Aqua-Farms, where oyster farmers teach visitors about harvesting cage-cultured oysters and the unique characteristics of those grown in Virginia, which have a deeper cup than some other varieties. The tour begins in the hatchery and follows the life stages through maturity, at which point you can try your hand at harvesting a few (40 cents each; no shucking service) and scrubbing them clean before tasting them while they’re still cold from the water.
Paddle over cages of maturing oysters in peaceful Nassawaddox Creek with Southeast Expeditions on a tour ($85 per person, including a bottle of wine for each couple) that takes you to Chatham Vineyards, set on a historic farm that dates back four centuries. After tying up the kayaks, sip glasses of steel-fermented Chardonnay and, on designated winter Sundays (or by request), take a seat next to the outdoor fire pit and enjoy oysters that the staff pulls from the cold waters of Church Creek.
Follow an unofficial oyster trail to taste the different flavor profiles from Virginia’s seven distinct growing regions, including briny, deep-flavored specimens grown in the Atlantic to balanced, slightly sweet oysters grown in the bay. Start at the northern edge of the Eastern Shore at Don’s Seafood Restaurant on Chincoteague Island to sample options from the raw bar, such as Tom’s Cove bayside oysters ($6.29 for a half-dozen). Drive south to the historic wharf town of Onancock, where local Shooting Point Salts are served on the half shell ($7.99 for a half-dozen) at the Blarney Stone Pub. Finish the crawl by going straight to the source of H.M. Terry’s Sewansecott oyster operation in Willis Wharf (50 cents each; no shucking service). Look for the big, green sign, and buy a box of these rich, balanced bivalves for significantly cheaper than restaurant prices.
4. Insider’s Tip
Shucking has a reputation for being a difficult chore—but there is a secret to opening local cage-cultured oysters. Ann and Tom Gallivan, the owners of Shooting Point Oyster Company (which sells to Maison Premiere), recommend opening their oysters from the bill end, not the hinge. Farmed Virginia oysters like their Shooting Point Salts have deep cups and thin shells, so approach shucking with scissors first instead of a knife. Cut away the brittle, fine edge of the oyster to reveal a space between the oyster lid and the cup. Then it’s easy to finish the job—you could even use a butter knife.
5. Oddball Day
Shift your focus away from oysters to enjoy some of the Eastern Shore’s other pleasures. Start the day at the Cape Charles Coffee House, where homemade blueberry muffins ($2.25) are served straight from the oven along with bottomless cups of strong coffee ($1.50). Leave the Eastern Shore briefly to drive over the 23-mile Chesapeake Bay Bridge-Tunnel, an engineering marvel when it opened in 1964 and still striking today. Cruising along, the bridge appears to suddenly end—as if it’s yet to be completed—making for an exhilarating ride across bridges and down through tunnels beneath the water. Loop back toward the Eastern Shore and stop to savor the 360-degree views of the Chesapeake Bay from the edge of a wooden fishing pier at Virginia Originals (you can find a wide selection of local wines inside). Next, follow the locals into Sting-Ray’s, a roadside greasy spoon serving up local seafood such as crab cakes ($22) and fried catfish ($15). Then, catch some air at the Eastern Shore Hang Gliding Center (from $149 for twenty minutes; by appointment, weather permitting), where a specially designed aircraft will lift you and an instructor to either 2,500 or 4,000 feet over the rural landscape. Back on the ground, have a hearty dinner at Bill’s Prime Seafood & Steaks. There are more oysters to be had—Chincoteague salts ($8.50 for a half-dozen)—or you could skip seafood altogether and opt for herb-roasted prime rib ($25). Finish the night with a craft beer ($5) in Cape Charles at Kelly’s Gingernut Pub, a local favorite located in a historic building that was formerly a bank. Ask for a table inside the original vault complete with a heavy steel door.
Find the latest news on seafood festivals, special winery events, and birding opportunities on the Eastern Shore Tourism site.
Learn about one family’s story growing oysters in the Eastern Shore over the course of four generations. You can conveniently order their Sewansecott oysters to be shipped to your home as well.
Find out how Virginia oysters are grown sustainably and actually contribute to the health of the local environment on this website, created by the Virginia Marine Products board.