Spanning 70 miles and bordered by the Chesapeake Bay and the Atlantic Ocean, Virginia’s Eastern Shore is a coastal paradise. The waterfront region is one of the best-kept secrets in the Commonwealth, boasting gorgeous beaches, incredible wildlife, and serene communities that welcome visitors to discover their quiet charm. If you’re looking for a beachfront break without the crowds, plan a vacation to one of these five small towns on the Eastern Shore.


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Centrally located on the Chesapeake Bay side of the Eastern Shore, Onancock is an inviting small town that was founded in 1680. Visited by Captain John Smith in the early 1600s, he wrote that the land was the “Gem of the Eastern Shore”. The town was historically a bustling port town, with steamboats traveling between Baltimore and Norfolk stopping in the waterfront community for supplies and rest. Today, the town is filled with stunning Victorian-era homes and local boutique shops. The only ferry to Tangier Island from the shore departs from Onancock, giving you access to yet another incredible small town on the Eastern Shore. If you’re in the mood for a little adventure, rent a kayak or stand up paddleboard from Burnham Guides, located in the historic Steamboat Ticket Office at Onancock Wharf.

Where to Stay/Eat: Book a stay at the Charlotte Hotel, a cute boutique retreat in the heart of downtown Onancock. Grab a bite to eat at Mallards at the Wharf, the only waterfront restaurant in Onancock.

Cape Charles

ES20030503V_014.JPGPhoto credit: Adam Lewis,  @adamtlewis

Just across the Chesapeake Bay Bridge Tunnel, Cape Charles is an idyllic small town that exudes endless character. The downtown area has lots of local shops carrying everything from handcrafted jewelry to homemade ice cream. Cape Charles is an excellent destination for wildlife lovers, as Kiptopeke State Park is right outside the town. SouthEast Expeditions offers an Aqua-Culture Clamming tour along Cherrystone Creek, just north of Cape Charles. Kayakers learn about aquaculture practices and tour a working clam farm, then hand pick their own clams straight from the Bay waters to sample the tasty results. Another great kayaking trip is the Paddle Your Glass Off tour, a guided paddling expedition through the Bay waters to Chatham Vineyards, where you’ll take a scenic break for a little wine tasting.

Where to Stay/Eat: Stay in the downtown area at the Hotel Cape Charles or The Bay Haven Inn and get a taste of the local seafood at either The Shanty or the Oyster Farm Seafood Eatery, followed by a little dessert at Brown Dog Ice Cream.


ES19031301V_005.TIFA small Atlantic island tucked away on the northeastern corner of Virginia’s Eastern Shore, Chincoteague is best known for the wild ponies found in the bordering Chincoteague National Wildlife Refuge. These beautiful animals were made famous in the book and subsequent movie, Misty of Chincoteague, and the town houses a museum that tells the true story behind the ponies. The small town draws visitors looking for a quiet coastal beach experience as well as space travel enthusiasts, as the NASA Wallops Island Flight Facility Visitor Center, NASA’s primary facility for suborbital missions, is just south of the island. The facility also has a free museum where you can learn about previous rocket launches and the science behind the missions. For a breathtaking view of the surrounding landscape, stop by the Assateague Lighthouse on the neighboring Assateague Island. Access to the top of the lighthouse is open to the public during select visiting hours.

Where to Stay/Eat:

Enjoy a stay in Chincoteague at the Channel Bass Inn Bed & Breakfast or the town’s first boutique hotel, the Marina Bay Hotel & Suites. Eat at Bill’s Prime Seafood & Steaks, followed by a few scoops at Island Creamery, ranked the best ice cream in America by TripAdvisor.


ES20030503V_014.JPGPhoto credit: Adam Lewis,  @adamtlewis

Wachapreague is a tiny Victorian-era town with a population of only 200 permanent residents, and is surrounded by farmland, woods, water, and some of the only undeveloped wetlands and barrier islands in the Mid-Atlantic. This sleepy coastal town is well known for sport fishing, bringing enthusiasts from around the world to fish in the vast and plentiful waters of the Atlantic Ocean. Bird watching is also a big draw, especially during spring and fall migrations when thousands of birds take flight through the region. Book a tour or rent a kayak to journey through Wachateague’s waters with Daytrippers, where you’ll explore the adjacent barrier islands, dig for clams, or try your hand at fishing.

Where to Stay/Eat:

The town’s most popular place to dine is the Wachapreague Island House Restaurant, and for an overnight stay you can either book a room at the Wachapreague Inn.

Tangier Island

Tangier Island lies twelve miles off the western coast of the Eastern Shore in the Chesapeake Bay and is known as America’s “Soft Crab Capital”. The town’s small population mainly work as watermen, harvesting fresh seafood from the surrounding Bay waters. These watermen have been working the rich waters of the Chesapeake Bay for generations, and their deep roots are apparent in the unique dialect spoken on the island, a form of English not heard anywhere else in the world. The remote island is only accessible by plane or boat, with a ferry bringing visitors from Onancock on the Eastern Shore and Reedville from the mainland, and the island’s inhabitants travel Tangier’s short series of roads by foot, bicycle, or golf cart. Visit the Tangier History Museum to learn about the small island’s long and captivating history.

Where to Stay/Eat:

Sample fresh seafood at Lorraine’s Seafood Restaurant. If you’re interested in staying overnight, book a stay at the Bay View Bed & Breakfast.

Virginia has dozens of small towns that offer endless charm, hospitality, and memorable adventures. Whether you visit a small town for outdoor lovers or head to the best foodie destinations, Virginia’s charming small towns welcome you to discover a unique vacation experience.