Here's Why Captain John Smith Called This Chesapeake Bay Town The Gem Of The Eastern Shore

When Captain John Smith sailed from the new settlement of Jamestown to explore Chesapeake Bay in the summer of 1608, he didn’t know that he was mapping the largest estuary in North America. In two explorations that year, Captain Smith documented some 3,000 miles of the Bay and its tributaries, as well as Native American villages and the region’s plentiful natural resources. Published in 1612, the “Smith Map” was the go-to guide to the region for decades.

Yet, despite seeing thousands of miles of shoreline, there was one place in particular that stood out: Onancock Creek and its natural harbor. So impressed was he that he declared it “the Gem of the Eastern Shore.”

It was a label that would prove remarkably prescient. Established in 1680 as one of King James' original 12 royal colonial ports, the town of Onancock quickly established itself as a vital commercial hub. Safely tucked away four miles inland from Chesapeake Bay, Onancock Wharf not only provided shelter from storms but also had a deep natural harbor that would serve Virginia shipping and trade for over 250 years.

The Gem of the Eastern Shore

Smith’s intuition about Onancock’s potential as a harbor was proven right again during the American Revolution. Not only did it serve as home to militia barracks, but it also played a crucial role in naval engagements.

In November 1782, 13 months after Cornwallis' surrender at Yorktown, local volunteers assisted with a campaign against British barges harassing Chesapeake Bay farms. Despite the fact that the ensuing Battle of Kedges Strait saw three of four American barges retreat under heavy fire, it was to be the last naval action between the fledgling United States and the mighty British Empire.

By the mid-19th century, Onancock had also become a stop along the stagecoach route between Wilmington, Delaware, and the Virginia town of Eastville. It also later served as a port of call for steamboats carrying passengers and goods between Virginia and Baltimore until well into the 20th century.

Onancock Historic District

Visit today, and it’s very apparent that Onancock wears its maritime heritage and Revolutionary War history with pride. While Captain Smith wouldn’t recognize the place today (except perhaps for the views over Chesapeake Bay), many of those who were around in the town’s early years would. Paying a visit is a truly authentic Eastern Shore experience, with watermen still heading out early each morning to harvest blue crabs and oysters from the Bay, and many buildings from the town’s early years are still around to be enjoyed

Ker Place is one such structure. Built in 1799 for a prosperous merchant farmer, this exquisite red-brick, Georgian-style mansion now operates as a museum, complete with period-furnished rooms and details of the home’s history. A maritime display includes an original oyster boat built in 1904 that was used by local watermen right up until the 1960s. Guided tours are available, but even if the museum is closed, the grounds are worth a wander.

At the other end of the Onancock Historic District, the Onancock Wharf & Marina features a view that Captain Smith would recognize. Standing on the boardwalk with the marina at your back, Onancock Creek stretches out before you as it winds its way to Chesapeake Bay. Behind you, the 19th-century Hopkins & Bros. Store is now home to the top-notch Mallards at the Wharf restaurant and one of the state’s best patio sunsets (reservations recommended).

As you stroll through the Onancock Historic District, you’ll also wander past five 19th-century churches, all of them on Market Street (the town’s Main Street). These include Cokesbury United Methodist Church, now a cultural center, and Holy Trinity Episcopal Church, considered one of the prettiest Gothic churches in Virginia.

Arts and Culture

Captain Smith would also have approved of Onancock’s cultural offerings, too. The North Street Playhouse provides a year-round schedule of professional theater productions, including original musicals, while the historic Roseland Theatre has been screening first-run and independent movies since 1950.

The newly refurbished Historic Onancock School building on College Avenue, just a short stroll away from the downtown area, is a must-visit. Opened in 1921, the town has repurposed the school as a cultural center that now houses everything from artist studios and galleries to dressmakers and craft shops. It’s fun to wander the old school hallways, checking out the historic displays, and popping in and chatting with local entrepreneurs and creators.

The town's Second Friday Art Stroll is another great reason to visit the school as well as Downtown Onancock. Held year-round for over 20 years, it’s an excellent opportunity to explore the local cultural scene with extended gallery hours, guest artists, live music, and wine tastings.

Watery Fun

That natural deep-water harbor that so impressed Captain Smith is now a hub of recreational boating fun and commercial fishing. Bring a boat of your own, and you can dock it at the town wharf.

If you’re boatless and want to get out on the water (and you should), the good folks at Burnham Guides Paddle & Bike offer kayak rentals and paddleboarding equipment to explore Onancock Creek. They also provide guided kayak tours that provide insight into the area's unique Bay ecosystem, getting you even closer to the kind of scenery Captain Smith would have seen over 400 years ago.

One of Chesapeake Bay’s most popular water-based excursions also departs from the town wharf: the Tangier-Onancock Ferry. Operating from May through October, this locally owned ferry provides the opportunity to explore Tangier Island, an inhabited Bay island that’s famous for its crab-fishing and distinctive culture. For a shorter Bay trip, Holly Cove Charters offers fun sunset cruises on the Chesapeake Bay.

Dine Local, Stay Local

There’s no shortage of excellent places to eat in Onancock, either. The Blarney Stone Pub, a friendly, locally owned tap house, is popular not just for its tremendous choice of craft beers, but also for menu staples like beer-battered fish and chips, bangers and mash, and delicious bar pizzas.

For an upscale meal, The Charlotte Hotel dates from 1907 and features dishes prepared with Eastern Shore produce and fresh seafood. Its boutique-style accommodations make for an ideal base from which to explore the town.

The Inn at Onancock, housed in a charming 1886 Victorian-era home just off Market Street, is a personal favorite. Featuring cozy guest rooms with en suite bathrooms, the freshly made gourmet breakfasts are delicious. Be sure to accept the invitation to attend the inn's 5 pm Wine Down with tasty hors d'oeuvres, local wines, and the opportunity to connect with the innkeepers for tips and tactics regarding local places to visit (it was they who suggested the pizza at Barney Stone, Mallards’ sunset patio, and the Historic Onancock School).

Captain John Smith Was Right

Pay a visit to Onancock today, and you’ll certainly find yourself agreeing with Captain John Smith's 400-year-old assessment of the area. This authentic Chesapeake Bay town serves up a fascinating dose of maritime heritage mixed with Eastern Shore hospitality that makes it an awesome place to visit. Yes, Captain Smith: the Chesapeake Bay town of Onancock is definitely the Gem of Virginia’s Eastern Shore.