8 Underrated 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 winding coastline bordering the states of Maryland and Virginia. Chesapeake Bay is fed primarily by the Susquehanna River in Pennsylvania and flows into the Atlantic Ocean at Hampton Roads in Virginia. It is both a vital commercial waterway and one of America’s greatest natural wonders. In addition to a few major port cities, there are also many beautiful little towns along the bay, and we’ve rounded up some underrated gems that deserve a spot on your next travel list.

Saint Mary’s City, Maryland

Colonial ship at the St. John's Site Museum, Historic St. Mary's City, Maryland, USA.

Colonial ship at the St. John’s Site Museum, Historic St. Mary’s City, Maryland, USA. Editorial credit: Regine Poirier /

Located near the southern tip of the western shore of Chesapeake Bay, Saint Mary’s City was founded in 1634 as the first English settlement and colonial capital of Maryland. The city’s historic downtown, home to approximately 1,000 full-time residents, has been restored into a “living history” area similar to Williamsburg, Virginia, with rebuilt buildings, historical interpreters and four museums. More history awaits at the adjacent Saint Mary’s College of Maryland, a long-standing institution that houses one of the country’s most important archaeological field operations. The town is also surrounded by nature trails and a beautiful bay, including a replica of a sailing ship from 1634.

Salisbury, Maryland

Aerial view of the Salisbury City Park bridge and lake during the fall, Salisbury, Maryland.

Aerial view of the Salisbury City Park bridge and lake during the fall, Salisbury, Maryland.

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

Cambridge, Maryland

Lighthouse and marina in Cambridge, Maryland, during the fall.

Lighthouse and marina in Cambridge, Maryland, during the fall.

Founded at the mouth of the Choptank River in 1684, Cambridge is one of Maryland’s oldest seaports. The current city of about 13,000 inhabitants honors this maritime history with a large number of historical monuments, museums and guided walks. Additionally, Harriet Tubman, a famous leader of the Underground Railroad who led escaped slaves to freedom, was born nearby and is now honored with a museum downtown. Cambridge has beautifully combined this look at the past with a focus on the future, with revitalization efforts that have transformed the downtown area. It’s no wonder that Cambridge is often rated as one of the most livable small cities in America.

Cape Charles, Virginia

Aerial view of Cape Charles, Virginia, looking northeast from the Chesapeake Bay, showing a visible grid pattern.

Aerial view of Cape Charles, Virginia. Editorial credit: Kyle J Little /

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

Chestertown, Maryland

Aerial view of Colonial Chestertown on the Chesapeake Bay, Maryland, USA, during the summer.

Aerial view of Colonial Chestertown on the Chesapeake Bay, Maryland, USA.

Chestertown was founded in 1706 just upstream from the mouth of the Chester River, and this city of 5,000 residents is full of historical gems related to the American Revolution era. A reproduction of the Sultana, a 1768 schooner, welcomes visitors like a museum on the water. Sailing ships come from far and wide for the annual Tall Ship and Wooden Boat Festival, and the city hosts an annual reenactment of the lesser-known 1774 ‘tea party’ protest against British taxation. Additionally, Chestertown is home to the first college chartered in the independent United States, Washington College (founded in 1782). This historic institution fits in nicely with the numerous colonial and nineteenth-century buildings that can be found in the beautiful city center.

Urbanna, Virginia

Lansdowne, a historic home in Urbanna, Virginia.

Lansdowne, a historic home in Urbanna, Virginia. By Ryanlintelman, CC BY-SA 4.0, Wikimedia Commons

Urbanna, a town of 500, bustles with activity for a few days each November, when some 75,000 visitors come for the annual Virginia Oyster Festival. If you like great oysters but don’t like big crowds, come to this community at the mouth of the Rappahannock River at another time of year to enjoy great seafood restaurants like Walton’s or the Virginia Street Cafe. Founded in 1680, Urbanna once prospered as a tobacco port, and a walking tour offers views of numerous historic homes and businesses, such as the museum and visitor center housed in a colonial-era store. All the while, the inviting waters of the Chesapeake Bay beckon just a few miles downstream.

Oxford, Maryland

Aerial view of Oxford, Maryland on the Chesapeake Bay with clouds, water and coastline.
Aerial view of Oxford, Maryland, on the Chesapeake Bay with clouds, water and coastline.

Oxford and Annapolis were founded as Maryland’s first two seaports, while Oxford was founded on the East Coast in 1683. Although it hasn’t matched the size or fame of Annapolis, Oxford is a lovely town of about 1,000 residents that still has a busy waterfront, mainly 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 area, visit historic sites such as the Oxford Customs House and enjoy excellent seafood restaurants and boutique shopping. The Oxford-Bellevue Ferry, which has been in use in various forms since the city’s founding, takes visitors across the Tred Avon River to the equally beautiful town of Bellevue.

Stevensville, Maryland

Church in Stevensville, Maryland.
Church in Stevensville, Maryland.

Stevensville is the largest community on Kent Island, the largest island in the Chesapeake Bay, covering approximately 31 square miles. Kent Island was once an important ferry terminal, with Stevensville serving as the central station for the short railway line 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 have been transformed into tourist destinations and bedroom communities in Annapolis, yet Stevensville has done an excellent job of preserving the historic character of a railroad town. Nearby highlights include Terrapin Point Public Beach, Ferry Point Nature Park, and the Kent Narrows dining and entertainment district.

Discover the hidden gems of Chesapeake Bay

Chesapeake Bay has largely recovered from decades of industrial pollution and has once again become a top destination for water sports, sightseeing and historic tourism. Many of the bay’s communities date back to the colonial era, but have also adapted to become modern tourist destinations. While larger travel hotspots like Baltimore, Annapolis, and Williamsburg are worth exploring, take some time to visit some of the smaller and lesser-known cities that add to the beauty and vitality of the Chesapeake Bay.