The Route Less Traveled: Boating the Chesapeake Bay’s Eastern Shore

The Colonial town of Onancock has a half dozen eateries just steps from the harbor.

Chesapeake Bay boaters who typically head down along the western shore are missing out on two delightful waterside towns along the Eastern Shore of Virginia.

Cape Charles and Onancock, two walkable towns along the 70-mile Virginia Chesapeake Bay coastline, have growing numbers of restaurants, shops and hotels just steps from the town harbors.


Virginia’s Eastern Shore is only three hours by car from Washington D.C., but it’s a world apart. Settled in the early 1600’s, the region was isolated from mainland America for four hundred years, until the convenience of rail, then cars, made it a bit more accessible. The Chesapeake Bay Bridge-Tunnel connected the southern tip to mainland Virginia in the mid-60s.

Things have changed slowly on the Eastern Shore of Virginia over the centuries. Today the culture is a rich mix of families with roots that are hundreds of years old and an influx of escapees from the big cities to the north.

In some ways, modern America has barely touched down on the Virginia Eastern Shore — there are few corporate chain restaurants and hotels but lots of family-owned places. Cell phone connectivity can be spotty, and nobody is in much of a hurry. In other ways, the future of America is here — NASA has been launching missiles at Wallops Island since 1945, and it’s well worth a visit to the Wallops Island Visitor Center.


A small boutique hotel just a short walk from the harbor, the Charlotte serves dinner only.

Just southeast of Tangier Island, Onancock is approached along the five-mile Onancock Creek lined with majestic homes. Once you dock, stop in at the harbor office and pick up information about the town, including a walking tour guide. Go no further than a few steps to Mallards on the Wharf for a meal overlooking the water or walk up the hill to the town center and you’re at one of the Virginia Eastern Shore’s culinary crossroads. Choose from an upscale bistro, an Italian kitchen, an Irish pub, a casual cafe open for breakfast and lunch only, and two dinner-only boutique inns: The Inn and Garden Cafe and the Charlotte Inn and Restaurant. Get to the Corner Bakery early enough for their signature donuts.

Hunt for treasure at boutiques and antique stores and pick up some goodies at the North Street Market.  Enjoy a short walk to Ker Place, an elegant Federal-period estate, and the Virginia Eastern Shore Watermen’s Museum and Research Center. Both tell the story of America from its earliest founding days. If you’re in the mood for a night on land, B&Bs are tucked away down neighborhood streets. You can catch the latest movie at the quaint 1950s Roseland Theater; it has a state-of-the-art digital sound system. Or take in a live show at the North Street Playhouse.

Pull out your walking tour guide and head across the bridge nearest the harbor to Mount Prospect, a neighborhood overlooking Onancock Creek and enjoy the quiet, tree-lined streets anchored by the circa 1790 Prospect Hill estate.

If you haven’t been to Tangier Island yet, catch the Tangier ferry May to October right at the Onancock harbor.

Learn More About Onancock
Onancock on Trip Advisor
Reserve the Onancock Harbor and Wharf Here


Gaze out over the Chesapeake Bay at the Oyster Farm and Seafood Eatery.

Near the southern tip of Virginia’s Eastern Shore on the Chesapeake Bay, Cape Charles is a relaxed, cheerful beach town with a free beach that’s steps from the town harbor and bustling town center. Breakfast or lunch at the Cape Charles Coffee House and shop along the main street, Mason Avenue — don’t miss Watson’s Hardware — it’s well stocked with everything from tools to beach toys.

The half-mile Cape Charles beach is just steps from the town center’s shops and restaurants.

The boutique Hotel Cape Charles looks out over the harbor, and stately Victorian B&Bs line the neighborhood streets nearby. Walk the trails at the Eastern Shore of Virginia Wildlife Refuge, a short drive from Cape Charles. An art deco theater spotlights local, regional, and national talent. The Oyster Farm at Kings Creek, with a marina, restaurant and event venue, flanks the northern side of town, and Bay Creek Resort & Club on the southern side is home to two nationally ranked golf courses designed by golf legends Jack Nicklaus and Arnold Palmer.
Learn More About Cape Charles
Cape Charles on Trip Advisor
Reserve the Cape Charles Town Harbor Here

You may also like: Nine Charming Small Museums on VA’s Eastern Shore
Six Great Beaches on Virginia’s Eastern Shore
An Adventurer’s Guide to 5 Days on Virginia’s Eastern Shore

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