It may no longer be a “best kept secret” (thanks a lot, Internet!), but Virginia’s Eastern Shore, a 70-mile strip of coastal magic situated between the Chesapeake Bay and the Atlantic Ocean, remains a place where you can experience the very best of small-town America on your way to truly getting away from it all.

From the small-town charm of Cape Charles and the famed ponies of Chincoteague to the old-world sights and sound of Tangier and the literal rockets’ red glare of Wallops Island, the Eastern Shore offers a wealth of experiences that allow you to downshift to vacation gear and stay there a while.  

Cape Charles

The first attraction of this one-time fishing village comes before you ever touch its shores. You arrive via the Chesapeake Bay Bridge Tunnel, a 17.5-mile miracle of engineering and construction that takes you above and beneath the Chesapeake Bay while offering breathtaking views all the while. Once you hit solid ground, Cape Charles, founded in 1884 by Pennsylvania Congressman William L. Scott (Erie) and New York Penn railroad man Alexander Cassatt, is a visitors’ delight where Victorian architecture mixes with all the small-town charm you can handle and then some, not to mention gorgeous beaches, great dining and some of the best darned ice cream you’ll ever consume.

Places to Stay

Everything old is new again at the historic-yet-modern Hotel Cape Charles (hotelcapecharles.com), a mainstay of the hospitality landscape there for more than a century. Its 23-rooms are full of contemporary touches, including rooms and common spaces full of natural light and private glass balconies that offer up gorgeous harbor views. The Northampton Hotel (https://thenorthampton.com) features beautiful ensuite rooms offering all the comforts of the finest modern hotels while retaining the building’s historic look and feel. Vacation home and apartment rentals aboundthroughout the island, as do bed-and-breakfasts, including the lovely 5-room Bay Haven Inn (bayhaveninnbnb.com).

Beach life doesn’t get much better than on Cape Charles’ lovely and calming shores, accessed just steps from its charming downtown

Seay Stories Sportfishing offers inshore, offshore and deep sea fishing. Burnham guides kayaking with the Norfolk Academy. Photos Courtesy of Eastern Shore of Virginia Tourism

Activities

Beach life doesn’t get much better than on Cape Charles’ lovely and calming shores, accessed just steps from its charming downtown. Looking to get out and throw a line in the water? Your first stop is Bailey’s Bait and Tackle (baileysbaitandtackle.com), right on Mason Street, then it’s an easy walk to the town pier, where you can try your luck and where you’ll see charters aplenty in the harbor just waiting to carry you out into the bay and/or ocean, including  Seay Stories Sportfishing (seaystoriessportfishing.com). And for those who want to combine two favorite activities, try “Paddle Your Glass Off,” a kayak/wine tour from Southeast Expeditions (southeastexpeditions.com) that takes you by water to Chatham Vineyards!

Dining and Entertainment

Craft brewing is a family affair at Cape Charles Brewing Company (capecharlesbrewing.com), run by brothers Mark and Chris Marshall along with their mom, Deborah, and featuring a massive array of brews and a delicious menu. Cape Charles Distillery (ccdesva.com) is another wildly popular spot, famous for its inventive craft cocktails. Dining options are highlighted by the Hook @ Harvey, located at the mouth of the town harbor and combining stunning water views with a high-end seafood dining experience. The Oyster Farm (theoysterfarmatkingscreek.com) is a 39-acre restaurant/marina/event center/resort that offers the very best in water-to-table dining. Locals and visitors alike flock to The Shanty (shantyseafood.com), a Cape Charles harbor-front classic serving up stunning nightly sunsets along with a sumptuous seafood menu that includes something for everybody. No talk of food in Cape Charles is complete without the Brown Dog (browndogicecream.com), the classic ice cream shop that serves up pure delicious Americana one scoop at a time.

Wild ponies run on Chincoteague Island, while the serenity of Onancock Wharf awaits. Photos Courtesy of The Virginia Tourism Corporation

Chincogteague/Assateague

Chincoteague is known as the gateway to the Chincoteague National Wildlife Refuge, which is just across the water in Assateague. That is where the ponies are gathered each year and ridden by saltwater cowboys across to Chincoteague, where they are famously celebrated and paraded through the streets before being sold at auction. It’s a tradition that dates back to 1922, when the local fire department was looking to raise funds after a pair of catastrophic blazes. The spectacle has drawn huge crowds ever since, but if you only focus on the equine attractions, you are really missing out on some of the most pristine beaches on the East Coast, surf-fishing for days, on a sprawling wildlife refuge that offers a migratory stop for more than 300 varieties of birds, on endless oyster beds, nature cruises, hiking, biking and on a front-row seat to NASA’s Wallops Island Flight Facility, where missions include Antares rockets heading  to resupply the International Space Station. When in Chincoteague, try Bill’s Prime Seafood & Steaks, which has been serving up breakfast lunch and dinner on the island since 1950 and is known for hand-cut steaks and legendary desserts, and for opening at 5:00 AM each day to serve the local watermen. Looking for some adventure? Try Chincoteague Island Adventures (chincoteagueislandadventures.com) for all your boating, pony-watching and waterfowl hunting needs!

Onancock

Labeled the “gem of the Eastern Shore” by Captain John Smith in the 1600’s, Onancock has served as an important port for commercial and pleasure boats alike while earning a reputation as one of the Mid Atlantic’s most charming escapes. With gorgeous seascapes combined with an eight-block downtown full of lovely shops, restaurants and more, this gem seems to get better and better. For adventure, try Burnham Guides (burnhamguides.com). They are the only outfitter on the Eastern Shore of Virginia that does overnight kayak and fishing trips that take you around the barrier islands. Spend a night or two at the charming Inn at Onancock, and try out Mallards at the Wharf (eatatmallards.com), where owner Johnny Mo, aka “Johnny Mo the Musical Chef,” might just cook up a tune on his guitar once he is out of the kitchen!

There’s more…much more, including the bygone-era magic of no-cars-allowed Tangier Island…but we’ll leave some to your imagination and for your own discovery. Suffice to say, the Eastern Shore of Virginia is ready and waiting for you and will not disappoint! 

For more information on creating your Eastern Shore of Virginia experience, go to VisitESVA.com.

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