7 Must-Visit Small Towns In Chesapeake Bay

The largest estuary in the United States and one of the biggest in the world, Chesapeake Bay has been a vital waterway for fishing, trade, industry, travel, national defense, and recreation for centuries. Bordered by the mid-Atlantic states of Maryland and Virginia, the Chesapeake stretches from the Susquehanna River, coming from Pennsylvania to the Atlantic Ocean in the Hampton Roads region of Virginia. In addition to a few cities, most notably Baltimore, numerous small coastal towns sit along the Chesapeake’s winding shoreline. Among these many little gems, we have chosen seven must-visit Chesapeake small towns that need to be on your travel list.

Cambridge, Maryland

Cambridge, the seat of Dorchester County with a population of about 13,000, has been a seaport town situated at the mouth of the Choptank River since 1684. Cambridge’s maritime past is well-represented by numerous historical markers, museums, and guided walking tours. Speaking of history, Cambridge was the birthplace of a key figure during the Civil War era, Harriet Tubman. Tubman was a leader of the Underground Railroad who guided escaped African-American slaves to freedom, and her contributions are documented at an excellent Cambridge museum dedicated to her. Along with honoring its past, Cambridge has revitalized its downtown area and hosts events like an annual regatta in June and Taste of Cambridge in October.

Cape Charles, Virginia

Cape Charles only has about 1,000 residents, but it sits at one of the most prominent points of Chesapeake Bay—the southern tip of the Delmarva Peninsula at the bay’s entry into the Atlantic Ocean. Home to the tallest lighthouse in Virginia, Cape Charles is also the first stop north of the Chesapeake Bay Bridge Tunnel, which has spanned the 17-mile mouth of the bay since 1964. But Cape Charles deserves more than just a quick stopover. The town is renowned for having one of the best collections of Victorian-era homes in the region, making it perfect for a walking tour that concludes at Cape Charles’ postcard-pretty town beach.

Chestertown, Maryland

Chestertown, established in 1706 and the seat of Kent County, sits near the entry point of the Chester River into Chesapeake Bay. This town of 5,000 is overflowing with historic charm, with several colonial-era buildings and the campus of Washington College, chartered in 1782 as the first new college in the independent United States. Several years before that, in 1774, Chestertown residents held a “tea party” protest against British rule, an event which is re-enacted each year along the picturesque and very walkable waterfront. Chestertown also hosts an annual Tall Ship and Wooden Boat Festival, and the waterfront is home to a floating museum—a reproduction of the 1768 schooner Sultana.

Urbanna, Virginia

Oysters may not be the first thing to come to mind when you think of Virginia, but some 75,000 people flock to the tiny town of Urbanna (population 500) each November for the fantastic Virginia Oyster Festival. While the local oysters bring crowds today, Urbanna was founded near the mouth of the Rappahannock River in 1680 as one of colonial Virginia’s primary tobacco ports. Pleasure boats have long since replaced tobacco boats along the waterfront, which is now a great place for a scenic walk and dinner. Be sure to extend your walking tour into the downtown area as well, which contains historic homes and shops like R.S. Bristow’s (established 1876) and Marshall’s Drug Store.

Oxford, Maryland

Unlike some Chesapeake Bay towns, where pleasure boats have taken over the waterfront area, Oxford still has numerous commercial fishing boats unloading the catch of the day. It is fitting for Oxford to still have a commercial waterfront since the town was founded in 1683 as one of colonial Maryland’s first ports. Check out the restored colonial-era customs house near the waterfront, then venture into the quaint downtown for a walking tour among historic homes and shops. To add to the historic feel of your visit, take a trip across the Tred Avon River on the Oxford-Bellevue Ferry, in operation since the town’s founding, to the town of Bellevue, a historically African-American coastal community.

Williamsburg, Virginia

Few, if any, towns in America have capitalized on having a long history as effectively as Williamsburg, founded in 1632 on the Virginia Peninsula between the York River and James River. The town is world-famous for Colonial Williamsburg, a 300-acre living history museum consisting of hundreds of refurbished or rebuilt colonial-era structures staffed by knowledgeable re-enactors. Visitors are welcome to walk the grounds and admire the architecture and outdoor activities for free, while interior tours require a park admission fee. The College of William and Mary (founded in 1693) is located right near the historic area, and the other two “Historic Triangle” sites of Jamestown and Yorktown are short drives from Williamsburg.

Annapolis, Maryland

Annapolis rivals Williamsburg for historic preservation, although its long history has been preserved more organically. Established in 1649 and state capital since 1694, Annapolis’ low skyline is punctuated by the still-in-use 1779 Maryland State House on a gentle hilltop. The colonial-era streets that lead down to the stunningly beautiful Chesapeake waterfront look and feel much as they have for 300 years, albeit with numerous modern boutiques and eateries in the historic buildings. While exploring this Historic District, look for the historic markers documenting the history of African Americans in Annapolis. The town is also famous as the home (since 1850) of the United States Naval Academy along the mouth of the Severn River.

From the explorers and settlers of centuries ago to the vacationers of today, the Chesapeake Bay continues to draw in people with its convenient location and natural abundance. The small towns that encircle the bay, some of which have been there for more than 350 years, have changed with the times while continuing to maintain their historic character. So now is the time to plan your trip to the must-visit small towns of Chesapeake Bay!