These Small Towns in Chesapeake Bay Come Alive in Summer

The largest estuary in the United States and one of the largest in the world, Chesapeake Bay cuts a winding shoreline into the mid-Atlantic states of Maryland and Virginia. Fed by numerous rivers, most notably the Susquehanna (coming from Pennsylvania), Chesapeake Bay empties into the Atlantic Ocean in the Hampton Roads region of Virginia. Long a critical body of water for commerce, industry, fishing, and recreation, the Chesapeake’s shoreline is dotted with picturesque towns. While often sleepy in the winter, many of these towns truly come alive in summer, filled with visitors seeking a taste of the history, culture, cuisine, and natural beauty of Chesapeake Bay. 

Urbanna, Virginia

Unlike most towns on this list, Urbanna truly comes to life in November rather than in summer, with the annual Virginia Oyster Festival bringing up to 75,000 visitors to a town of only about 500 residents. That said, Urbanna is also a lively place throughout the summer months, with a beautiful downtown full of historic homes and businesses, making it a great place to go on a guided walking tour. Established in 1680 at the mouth of the Rappahannock River as one of Virginia’s primary tobacco ports, the town’s marina remains busy, now with pleasure boats instead of tobacco boats. Urbanna also hosts a monthly farmer’s market and an annual arts festival.

Oxford, Maryland

Situated on Maryland’s Eastern Shore along Chesapeake Bay, the little town of Oxford has a full-time population of fewer than 1,000. Although small, Oxford maintains a busy waterfront, especially during summer, with fishing boats unloading the catch of the day and sailboats unloading patrons of the town’s restaurants and shops. Founded in 1683, Oxford was established along with Annapolis as Maryland’s first two ports, and it maintains a restored colonial-era customs house and other historic sites. After spending a few hours walking the quaint downtown, visitors can take a trip across the Tred Avon River to Bellevue on the Oxford-Bellevue Ferry, which has been in operation in one form or another since 1683.

Mary’s City, Maryland

Founded in 1634 as the first English settlement in Maryland, St. Mary’s City is a small, utterly charming town of about 1,000 year-round residents. Located near the southern tip of the state’s Western Shore, St. Mary’s City’s historic town center has become a “living history” area, with reconstructed buildings, historical interpreters in period clothing, and four museums. Much of the rest of town is home to St. Mary’s College of Maryland, a public liberal arts institution with a sterling academic reputation. While much of the college crowd empties out during the summer, tourists seeking a taste of the town’s history, charm, and beauty more than make up for the loss.

Cape Charles, Virginia

Cape Charles, which has a population of around 1,000, is located just shy of the southern tip of the Delmarva Peninsula. The town’s summertime population swells with visitors, many of whom have crossed northward over the Chesapeake Bay Bridge Tunnel, which opened in 1964 and spans over 17 miles across the mouth of Chesapeake Bay. While small in size, Cape Charles is widely known for the impressive number of well-preserved Victorian era houses in town, which are reminders of its past as an important railroad and ferry terminal. Along with the many boutiques, galleries, and dining options downtown, Cape Charles has a charming town beach and abundant opportunities for kayaking, hiking, water sports, and more.

Chestertown, Maryland

Chestertown, founded in 1706, is located along the Chester River, which feeds into the Chesapeake Bay only a few miles downstream. Chestertown has a population of around 5,000, but that number swells with summertime tourists. The picturesque downtown area retains many colonial-era buildings and houses a lively arts and entertainment scene. On the waterfront, Chestertown has an annual Tall Ship and Wooden Boat Festival, as well as an annual reenactment of the town’s own 1774 “tea party” protest against British rule. A reproduction of the 1768 schooner Sultana is docked year-round as an on-the-water museum. Chestertown is also home to Washington College, the first new college chartered in the independent United States in 1782.

Cambridge, Maryland

Established in 1684 at the mouth of the Choptank River as a seaport, Cambridge is the seat of Dorchester County and has a year-round population of about 13,000. One of the downtown area’s top attractions is the Harriet Tubman Museum, named in honor of the local native and famous conductor of the Underground Railroad who guided enslaved African Americans to freedom. Cambridge also celebrates its maritime past with numerous museums, historical markers, and guided walking tours, yet also continues to reinvent itself for modern times. In recent years Cambridge has been rated one of the most livable small towns in America due in part to its revitalized downtown area that bustles with shops, restaurants, festivals, and farmer’s markets.

Williamsburg, Virginia

Williamsburg (population 15,000), founded in 1632 and located on the Virginia Peninsula between the York River and James River, is one of the oldest and most historic towns in the United States. The town’s modern-day claim to fame and summertime tourist draw is Colonial Williamsburg, a 300-acre living history museum made up of hundreds of restored or recreated colonial-era buildings and artifacts. The hundreds of thousands of annual visitors who come to Colonial Williamsburg also find plenty to explore in the rest of town, including many charming boutiques, galleries, and cafes. Williamsburg’s location also offers easy access to attractions like Busch Gardens, the Hampton Roads cities, and Virginia Beach.

Salisbury, Maryland

Salisbury, the largest town on Maryland’s Eastern Shore with a population of 33,000, sits near the border with Delaware on the Delmarva Peninsula between the Chesapeake Bay and the Atlantic Ocean. Due to this location, Salisbury serves as a gateway to Ocean City and Maryland’s other Atlantic beach towns. That said, Salisbury also has numerous attractions that draw visitors into the town itself, including the Salisbury Zoo and the monthly “Third Friday” festival held downtown. In addition to the summertime crowds, the presence of Salisbury University, a public college founded in 1925 with a current student population of 7,000, gives a welcome boost to the town’s commercial and cultural vitality.

Annapolis, Maryland

Established in 1649 and the state capital since 1694, Annapolis sits at the mouth of the Severn River and is a short distance from both Baltimore and Washington, D.C. Annapolis is one of the smallest but most beautiful state capitals in America, with a population under 40,000 and a stunning bayfront location. The United States Naval Academy has called Annapolis home since 1850. Starting at the still-in-use 1779 Maryland State House, Annapolis visitors stroll gently downhill through colonial-era streets full of shops, galleries, pubs, and restaurants to reach the stunning waterfront. Throughout this Historic District, Annapolis maintains many homes, buildings, and markers dedicated to preserving the history of African Americans in the area.

Having long since shed its past of industrial pollution, today’s Chesapeake Bay is one of the best tourist destinations in the United States for waterfront recreation and historical exploration. All around the Chesapeake Bay, old fishing villages, port towns, and industrial hubs have transformed into postcard-pretty bayfront communities. While they are great places to visit all year round, Chesapeake Bay’s most charming towns really come to life during the summer when the region’s beauty and vitality are at their peak.