Virginia’s Eastern Shore Islands, Stepping Back in Time

Island hopping for wild ponies and wine, oysters and outer space on Virginia's Eastern Shore

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Most of Virginia’s Eastern Shore—other than Virginia Beach—moves at a slower pace than the rest of the state. Take a weekend to live like a local and sample the casual elegance of the farmhouse inns, B&B’s, and waterfront resorts centered around a variety of outdoor activities. Land trusts protect much of the acreage from developers, and while the residents value their independence and privacy, visitors are warmly welcomed in the small waterfront towns.

Wine & Seafood

Stop by Chatham Vineyards and meet one of the local landowners passionate about preserving this slice of Virginia. Two generations of the Wehner family have put their expertise into the award-winning Chardonnay, Merlot, Cabernet Franc, Cabernet Sauvignon and Petit Verdot vines. Tastings often include pairings of Chardonnay with two varieties (bay and sea) of locally harvested Shooting Point Oysters, and you’re sure to get a warm welcome from Wilbur, the winery’s official canine greeter. Some of the local kayak tours also stop here for a tasting.

For lunch, grab local seafood at one of the many clam shacks along the way, most of which offer outdoor picnic-style seating.

Island Hopping on Virginia’s Eastern Shore

To really step back in time, to a place where residents are known for their unique English-Restoration-era dialect, take the ferry to Tangier Island, only accessible by boat. (Dogs are welcome on the ferry.) Stroll the small waterfront town to get a feel for the Eastern Shore’s fishing heritage. Seemingly untouched by time, you’ll see watermen going out in small boats for crab and oysters the way Eastern Shore fishermen have done for centuries.

Chincoteague Ponies

Wild ponies made famous by Marguerite Henry’s classic book, Misty of Chincoteague, roam Chincoteague National Wildlife Refuge and are cared for by the island’s local volunteer fire company. Legend has it that the ponies swam to shore in the 17th century from a Spanish galleon that sank nearby. On the last Wednesday and Thursday of July, the ponies are rounded up for the Annual Pony Penning and Auction, where some are sold at auction to benefit the town’s ambulance and fire services. Spend an afternoon crabbing, fishing, swimming, biking or hiking on this unspoiled island or strolling through the charming small town to see Misty’s commemorative statue. Pets are not even allowed in vehicles on the Virginia side of the refuge.

Outer Space

Interested in more contemporary history? America’s space program began at Wallops Island a decade before NASA was born, and research rockets still depart from here on a regular basis. Rockets resupplying the International Space Station also blast off from here. With a permanent museum and many special exhibits, Wallops is poised to become an international tourism destination for fans of the space program. To catch a rocket launch, check the website for launch dates.

Back on Land

Bird watchers will love the Eastern Shore of Virginia National Wildlife Refuge and Kiptopeke State Park, which also offers camping facilities and cabins. Both have great hiking trails and Kiptopeke also has a gorgeous beach, fishing and picnic facilities.

At A Glance

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