2025's Most Underrated Towns On The Chesapeake Bay

America's largest estuary, the Chesapeake Bay, has long appealed to adventurers. Located in the country’s Mid-Atlantic region and separated from the Atlantic Ocean by the Delmarva Peninsula, this lovely coastal region encompasses parts of Maryland and Virginia and is a popular place to visit for its many charming village-like communities.

While larger urban areas on the Bay, such as Baltimore and Annapolis, usually steal the limelight, the region’s smaller, often overlooked waterfront communities are far more likely to provide curious day trippers and weekend warriors with a more authentic Chesapeake experience. Choose wisely from these underrated towns in Chesapeake Bay, and you’ll find yourself immersed in places where life seems to continue much as it has for centuries.

Oxford, Maryland

Charming, tree-lined Oxford is one of the oldest towns in America and has a long and interesting maritime history. Already settled before its official founding in 1683, Oxford was to become one of the Thirteen Colonies' most important seaports and was a major player in tobacco exports right up to the American Revolution. While no longer used for international shipping, you can still get a sense of this seafaring tradition at the town dock where fisher folk can still be seen unloading their catches.

The Oxford-Bellevue Ferry provides another clue to the town’s reliance on the Bay. The oldest privately operated ferry service still in continuous use in the United States, it was established in 1683 and continues delivering passengers (and now cars, of course) to the west shore of the Tred Avon River. A journey of under 10 minutes, have your camera ready for spectacular shots of the river.

Other interesting things to do in this underrated town include exploring the Oxford Museum with its displays of over 300 years of local history and popping into the Scottish Highland Creamery for some homemade ice cream and fudge. Make a weekend of it with a stay at the Robert Morris Inn, dating to 1710 and boasting a restaurant serving fresh local seafood.

Cape Charles, Virginia

Over on Virginia’s Eastern Shore near the mouth of the Bay, Cape Charles was founded in 1884 and still displays its Victorian influences, especially in the Cape Charles Historic District. Home to one of the largest concentrations of turn-of-the-century buildings on the East Coast, it’s here you’ll find the Cape Charles Museum. Housed in a former power plant, it features exhibits on local history and the glory days of the railroad.

Cape Charles Beach is another must-visit attraction. It is the Eastern Shore’s only public beach that does not charge for admission or parking. Here, you’ll enjoy swimming, a public fishing pier extending into the Bay, and spectacular sunsets. Kiptopeke State Park is another beautiful spot. In addition to its sandy shoreline, it features hiking trails, boat launches, and excellent birdwatching opportunities.

Rock Hall, Maryland

Rock Hall is a fishing and boating town situated on the upper Eastern Shore of Chesapeake Bay that’s making a name for itself as a tourist destination. Originally called Rock Hall Cross Roads as it was part of the first road cut in Kent County in 1675, the town has maintained its waterfront character thanks to its fishing fleet which continues to harvest blue crabs, oysters, and rockfish. You can learn more about this traditional livelihood at the Waterman's Museum with its displays of related tools and tales.

Enjoy the great outdoors? If so, make sure you don’t overlook the Eastern Neck National Wildlife Refuge. Just a few miles south of town, this 2,285-acre refuge has well-maintained trails and is a layover spot for migratory birds each fall and spring. It’s also a nesting area for bald eagles and osprey.

As for the best time to visit, try to time it to coincide with the town’s Pirates & Wenches Fantasy Weekend in August. The town’s 4th of July weekend celebrations are also fun to experience, especially the waterside fireworks display.

Onancock, Virginia

Despite its small population, Onancock has plenty going for it. Its deep-water harbor has welcomed vessels since 1680, when it was established as one of the original colonial ports in North America. Today, the Onancock Wharf features floating docks and serves as the departure point for the Tangier-Onancock Ferry, which provides seasonal ferry services along with private sightseeing cruises.

Onancock has also made a name for itself as a quaint cultural destination, especially around the Onancock Historic District. Here, businesses like the Red Queen Gallery and Danny Doughty Gallery show off the work of local and regional creators, while the 100-plus-year-old Historic Onancock School now houses gathering spaces and artisan studios. Another cultural landmark, the North Street Playhouse, presents regular live theater productions, while the restored 1950s Roseland Theatre hosts first-run films and movie-related events.

St. Michaels, Maryland

Known as "The Town That Fooled the British" for its War of 1812 defense, St. Michaels is a must-visit Maryland destination. Start your adventure at The Chesapeake Bay Maritime Museum is a place you can easily spend a few hours exploring thanks to the Hooper Strait Lighthouse (built in 1879), a working boatyard, and exhibits on Bay traditions. For something completely different, pop into the LYON RUM//Windon Distillery for samples and take-home rum, while wine aficionados will want to visit St. Michaels Winery for its wines made from Maryland-grown grapes.

Wondering when to visit? The quirky Jack Russell Races in October is a good excuse, as is Christmas in St. Michaels, a weekend of fun events in mid-December. Round your visit off with a seafood meal at The Crab Claw Restaurant or Stars Restaurant at the Inn at Perry Cabin (you can also bed down for a night or two here).

Urbanna, Virginia

Held in early November, the Urbanna Oyster Festival provides the ultimate excuse to visit the east side of Chesapeake Bay. For two days, Urbanna sheds its usually under-the-radar character and sees up to 75,000 visitors turn this usually quiet town of just over 500 residents into a bustling hub of excitement.

In addition to vendors selling fresh seafood and oysters, local wine producers are also represented in this free but “pay-as-you-go” event. Other highlights include the Virginia Oyster Shucking Championship and unique VIP experiences. Other town highlights include Urbanna Town Marina, which offers slip rentals and charter fishing adventures.

If you can’t make it for the oyster festival, you can still get your fill of fresh local seafood at the Something Different Restaurant (try their crab cakes), or the waterfront Rappahannock Oyster Company’s Merroir Tasting Room.

The Final Word

Whatever you enjoy doing when traveling, these underrated Chesapeake Bay communities provide the kind of authentic small-town experiences you can’t usually find in more touristy places. Each has managed to preserve its unique character while offering traditional fresh seafood dishes, riveting maritime history lessons, as well as ample opportunities for outdoor adventure. Find out more by reading this list of 2025's most underrated towns in Chesapeake Bay.