Exploring Virginia's Beautiful Eastern Shore Is A Journey 400 Years In The Making
Virginia’s certainly not lacking in history. Dubbed the "Old Dominion" for its status as the British Empire’s first overseas territory, it was here that English settlers arrived nearly 420 years ago to lay the foundation for what would become the United States. Virginia’s Eastern Shore played a particularly important part in the country’s rapid growth. Just a year after helping establish Jamestown, the new colony’s first settlement, Captain John Smith set out to explore Chesapeake Bay, documenting over 3,000 miles of shoreline so that future settlers would have a fighting chance of success and survival.
More than four centuries later, Virginia’s Eastern Shore remains one of the Mid-Atlantic’s best-kept secrets. Bound by Chesapeake Bay to the west and the Atlantic Ocean to the east, this 70-mile stretch of the Delmarva Peninsula is a fascinating journey through American history that few other destinations can match.
Captain Smith’s Eastern Shore Gem
Of the seemingly endless shoreline Smith mapped, one area stood out for its potential as a port. Set four miles inland from Chesapeake Bay along Onancock Creek, Smith discovered a deep natural harbor here that was so well-suited to settlement that he declared it “the Gem of the Eastern Shore.”
Smith’s intuition was spot on. Established in 1680 as one of King James’ 12 royal colonial ports, Onancock quickly became a vital commercial hub, its deep natural harbor serving Virginia’s trade routes for over 250 years. By the mid-19th century, Onancock had become a stop along the stagecoach route and later served steamboats carrying passengers between Virginia and Baltimore.
Visit Onancock’s waterfront today and you’ll get a sense of just how Smith must have felt as he took in those same views all those years ago. Now a haven for kayakers, small pleasure craft, and fishing vessels, Onancock Wharf is a delight to explore. The 19th-century Hopkins & Bros. Store is a reminder of the harbor’s former importance, and though the ferries of old are long gone, you can still take a cruise from here to Tangier Island and its fishing community in the heart of Chesapeake Bay.
Other highlights of the Onancock Historic District along Market Street include Ker Place, an elegant Federal-style mansion built in 1799 that’s now a museum. For an authentic Eastern Shore stay, The Inn at Onancock, a charming B&B set in a Victorian home dating from 1886, provides cozy guest rooms, delicious homemade breakfasts, and a fun daily “Wine Down” event on the porch where you can mingle with the owners for tips on exploring the town.
Cape Charles And The Railroad
As you drive the Eastern Shore, you’ll find yourself at times crossing over the old railway line that runs the length of the peninsula. Built in 1884, the New York, Philadelphia, and Norfolk Railroad extended its line through the region, with newer communities popping up around stations. These include Exmore, Parksley, and Cape Charles at the southern terminus, along with several others, which, now that the railways have gone, seem almost empty.
Built specifically for the railroad, Cape Charles is once again thriving. Laid out on a 27-block grid with avenues named for Virginia statesmen and streets for local fruits, the railway company constructed a harbor especially for freight barges and passenger vessels crossing the Bay to Norfolk. By the early 1900s, Cape Charles was handling millions of tons of freight, becoming the Shore’s largest community.
While construction of the Chesapeake Bay Bridge-Tunnel (CBBT) led to the demise of the ferry and the railroad in the 1960s, savvy townsfolk rallied to preserve the town's Victorian-era character. Now protecting one of the East Coast’s largest concentrations of heritage architecture, Cape Charles Historic District is a lot of fun to explore in foot.
Highlights include the Historic Palace Theatre, still entertaining locals and visitors after 80 years in business, and the Cape Charles Museum with its exhibits of the town’s railroad heritage and vintage railway cars. Peach Street Books is a delightfully quirky spot to visit. Set in an old gas station that wouldn’t look out of place in Disney World, this secondhand bookstore also features a great little coffee shop.
Chincoteague Island's Wild Ponies
At the northern end of Virginia’s Eastern Shore, Chincoteague Island is known for its small-town vibe, undeveloped beaches, great seafood… and those famous wild ponies. The wild ponies of Assateague Island carry centuries of folklore, with local legend suggesting they may have descended from horses that swam to shore after Spanish galleons ran aground. Newer research, however, points to a less romantic cause, claiming the ponies turned feral after colonial-era farmers set them loose to graze on barrier islands to avoid paying mainland taxes.
Whatever the case, the ponies’ habitat is now protected by the Chincoteague National Wildlife Refuge. While it is possible to visit year-round, those in the know time their visit to coincide with the Chincoteague Pony Swim, held on the last Wednesday and Thursday of July.
Crowds of spectators travel from far and wide to witness the Saltwater Cowboys, a group consisting mostly of local firemen, guide the herd of 150 ponies across the quarter-mile channel. The ensuing auction is itself a historic event that’s been taking place here for over 100 years.
You can learn more about the ponies and the swim, as well as the legendary Misty made famous in literature and movies, at the Museum of Chincoteague Island. The Island Theatre, where the movie version of Misty of Chincoteague premiered, still shows the classic movie during Pony Swim week.
Other Eastern Shore Historic Sites
The town of Accomac has been the seat of Accomack County since 1693. A unique window into colonial Virginia, the Accomack County Courthouse is still in use today. Check out the nearby Debtor's Prison, built in 1783 and one of only a handful left in America. St. James Episcopal Church, dating to 1838, replaced an earlier structure where parishioners have worshipped since 1665.
Eastville’s even older. The seat of Northampton County since 1680 and one of the oldest continuously operating courthouse communities in the nation, Eastville Historic District still has court records dating back to 1632 (they’re the oldest continuous court records in America).
A short walk from the courthouse, you'll find another Debtor's Prison, this one built in 1731; and the Old Clerk's Office housing documents that predate the founding of Jamestown.
Although a much more recent historical event, the opening of the Chesapeake Bay Bridge-Tunnel (CBBT) in 1964 is no less important to the Eastern Shore and Virginia as a whole. Extending 18 miles over and under America’s largest bay, this marvel of American engineering features two-mile-long tunnels, two high-level bridges, and four artificial islands that together have pumped millions into the local economy.
A Journey Worth Making
Virginia’s Eastern Shore has everything needed for those looking to enjoy an authentic slice of Old America in the country’s 250th birthday year. Walkable historic downtowns, long public beaches, fresh seafood, and endless swathes of unspoiled nature, are all part of the fun. Four centuries after John Smith declared Onancock Creek the Gem of the Eastern Shore, this magnificent peninsula remains one of America’s most authentic travel destinations.
