8 Underappreciated Towns to Visit in Chesapeake Bay

Chesapeake Bay is the largest estuary in the United States and one of the largest in the world, with its meandering shoreline bordering the states of Maryland and Virginia. Fed primarily by the Susquehanna River in Pennsylvania and emptying into the Atlantic Ocean at Virginia’s Hampton Roads, Chesapeake Bay is both a vital commercial waterway and one of America’s great natural wonders. Along with a few big port cities, many lovely small towns sit along the bay, and we have listed some underrated little gems that deserve spots on your next travel list.

Saint Mary’s City, Maryland

Saint Mary’s City, set near the southern tip of Chesapeake Bay’s western shore, was established in 1634 as the first English settlement and colonial capital of Maryland. Home to about 1,000 full-time residents, the town’s historic center has been restored into a “living history” area similar to Williamsburg, Virginia, with rebuilt structures, historic interpreters, and four museums. More history awaits at the adjacent Saint Mary’s College of Maryland, a longstanding institution that houses one of the nation’s premier archaeological field operations. The town is also surrounded by nature trails and a beautiful bayfront, including a replica 1634 sailing ship.

Salisbury, Maryland

Salisbury, with 33,000 full-time residents, is the largest community on the Eastern Shore, which is Maryland’s section of the Delmarva Peninsula that sits between Chesapeake Bay and the Atlantic Ocean. Salisbury serves as a gateway to Maryland’s major beach town, Ocean City, as well as those in southern Delaware. But there are plenty of reasons to stop for a while in Salisbury as well! For example, the Salisbury Zoo is impressive for a small community, and Salisbury’s monthly “Third Friday” festival nicely showcases the downtown area. The town is also home to the Eastern Shore’s largest college, Salisbury University, which has grown rapidly in recent decades and now has a student population of about 7,000.

Cambridge, Maryland

Founded at the mouth of the Choptank River in 1684, Cambridge is one of Maryland’s oldest seaports. Today’s town of about 13,000 residents honors this maritime history with a bevy of historical markers, museums, and guided walking tours. Additionally, Harriet Tubman, a famous leader of the Underground Railroad who guided escaped slaves to freedom, was born nearby and is now honored with a downtown museum. Cambridge has nicely mixed this eye to the past with a focus on the future, with revitalization efforts that have transformed the downtown area. It is no wonder, then, that Cambridge is often rated as one of the most livable small towns in America.

Cape Charles, Virginia

Before the completion of the Chesapeake Bay Bridge-Tunnel, which spans the 17-mile mouth of the bay, Cape Charles was an important railroad and ferry terminal at the southern tip of the Delmarva Peninsula. Today, as the first community off the northern edge of the bridge, Cape Charles is a popular but far-from-crowded tourist destination with about 1,000 year-round residents. Several well-preserved Victorian homes give the downtown area a nice touch of historic charm, and Cape Charles boasts the only truly free (no parking or entrance fee) public beach in the area. The town’s location at the mouth of the bay makes it ideal for fishing (especially on the Cape Charles Fishing Pier), windsurfing, parasailing, and other water sports.

Chestertown, Maryland

Chestertown was established just upriver from the mouth of the Chester River in 1706, and this town of 5,000 is full of historic gems connected to the era of the American Revolution. A reproduction of the Sultana, a 1768 schooner, welcomes visitors as an on-the-water museum. Sailing vessels come from far and wide for the annual Tall Ship and Wooden Boat Festival, and the town hosts a yearly re-enactment of its less-famous 1774 “tea party” protest against British taxation. Additionally, Chestertown is home to the first college chartered in the independent United States, Washington College (established in 1782). This historic institution blends in nicely with the numerous colonial and nineteenth-century structures that dot the lovely downtown area.

Urbanna, Virginia

Urbanna, a town of 500, bursts with activity for a few days each November as some 75,000 visitors come for the annual Virginia Oyster Festival. If you enjoy great oysters but not big crowds, come to this community set near the mouth of the Rappahannock River any other time of year to enjoy great seafood joints like Walton’s or the Virginia Street Cafe. Urbanna, founded in 1680, once grew wealthy as a tobacco port, and a walking tour offers sights on numerous historic homes and businesses, such as the museum and visitor’s center housed in a colonial-era store. All the while, the inviting waters of Chesapeake Bay beckon from just a few miles downriver.

Oxford, Maryland

Oxford and Annapolis were founded as Maryland’s first two seaports, with Oxford established on the Eastern Shore in 1683. While it has not matched Annapolis’ size or renown, Oxford is a lovely town of about 1,000 that still maintains a busy waterfront, serving primarily fishing boats in the morning and pleasure boats the rest of the day. Day-trippers come by water or land to explore the quaint downtown, check out historic sites like the Oxford Customs House, and enjoy excellent seafood dining and boutique shopping. The Oxford-Bellevue Ferry, in operation in various forms since the town’s founding, shuttles visitors across the Tred Avon River to the equally lovely town of Bellevue.

Stevensville, Maryland

Stevensville is the largest community on Kent Island, the biggest island in Chesapeake Bay, which covers about 31 square miles. Kent Island was once an important ferry terminal, with Stevensville as the central station for the short railway that crossed the island. All this changed with the 1952 completion of the William Preston Lane, Jr. Memorial Bridge (Chesapeake Bridge), which connects Kent Island to both Annapolis and the Eastern Shore. Both Stevensville and Kent Island transformed into tourist destinations and Annapolis bedroom communities, yet Stevensville has done an excellent job of retaining its historic railroad-town character. Nearby highlights include the Terrapin Point Public Beach, the Ferry Point Nature Park, and the Kent Narrows restaurant and nightlife district.

Discover the Hidden Gems of Chesapeake Bay

Chesapeake Bay has largely recovered from decades of industrial pollution to once again become a prime destination for watersports, sightseeing, and historical tourism. Many of the bay’s communities stretch back to the colonial era yet have also adapted to become modern tourist destinations. While bigger travel hotspots like Baltimore, Annapolis, and Williamsburg are well worth exploring, spare some time to visit a few of the smaller and less famous towns that add to the beauty and vitality of Chesapeake Bay.