7 Towns In The Chesapeake Bay With Vibrant Downtown Areas
The parts of Maryland and Virginia that surround the Chesapeake Bay, America’s largest estuary, are rich with maritime heritage and a delightful collection of small towns that are perfect for exploration. Many of these communities retain vibrant downtowns with quaint main streets and ample historic treasures, each town boasting its own unique flavor and inviting atmosphere. Get started on your Chesapeake travel plans with the following guide to seven vibrant downtowns.
Salisbury, Maryland
The 33,000 residents of Salisbury, the largest community on Maryland’s Eastern Shore, enjoy a bustling regional hub—it is the gateway to Ocean City (Maryland) and the Delaware beach towns—with its own lively downtown scene. The historic downtown area, centered around Main Street, is home to an array of local shops like Karma's Closet and fun eateries like Roadie Joes. The Salisbury Zoo is comparable in quality to those found in larger cities, and the town’s monthly “Third Friday” festival offers live music, local vendors, and family fun from April through November.
Chestertown, Maryland
Founded in 1706 and home to a replica 1768 sailing ship (the Sultana) that is now a floating museum, Chestertown is a treasure trove of American heritage. The downtown area along the picturesque Chester River includes historic buildings such as the beautiful Prince Theatre, home to the Garfield Center for the Arts. The annual Sultana Downrigging and Tall Ship Festival is a highlight each November, celebrating the town’s maritime heritage. Wander through antique shops, dine at charming bistros, and explore Washington College, founded in 1782 and the oldest college founded after America’s independence.
Urbanna, Virginia
Urbanna, a small town of 500 with a big personality, swells with up to 75,000 visitors in late fall during the annual Urbanna Oyster Festival. Much less crowded the rest of the year, this former tobacco port founded in 1680 offers a downtown area with antique shops, cozy cafes, and waterfront views of the Rappahannock River. Get the most out of your tour of the town’s historic district by starting at the Urbanna Museum and Visitor Center, then enjoy a bit of fine dining or pick up some fresh oysters at Walton’s or Shores & Ruark.
Cambridge, Maryland
Cambridge, a scenic town of 13,000 on the Choptank River, offers a charming downtown area rich with nearly 350 years of history. Stroll along High Street and throughout downtown to discover an array of local shops, including Black Water Bakery and Butterfly Boutique. The city’s historic district features beautifully restored homes and landmarks, most notably the Harriet Tubman Underground Railroad Museum. Cambridge also hosts a variety of community events, including the annual Dorchester County Fair. It is no wonder that Cambridge has been rated one of the most livable small towns in America!
Williamsburg, Virginia
Founded in 1632 and the longtime colonial capital of Virginia, Williamsburg is world-renowned for the 300 acres of living history at Colonial Williamsburg Historic Area. Walk the grounds of Colonial Williamsburg for free or pay for admission to get interior views of the lovingly refurbished and recreated colonial buildings. Modern Williamsburg’s lively downtown district, located adjacent to both the historic park and the College of William and Mary (established in 1693), blends twenty-first-century amenities with colonial-inspired architecture. The district includes more than 40 shops and eateries, with national retailers and local treasures like Wythe Candies standing side-by-side.
Annapolis, Maryland
Annapolis, the waterfront capital of Maryland since 1694, boasts a compact, very walkable downtown that offers an incomparable mixture of historic charm and contemporary vibrancy. Start your walking tour at the iconic 1779 Maryland State House, then stroll slightly downhill through the cobblestone streets of the historic district, where Georgian architecture and waterfront views abound. Stop at a local eatery like Chick & Ruth’s Delly and a boutique such as the Lucky Knot before ending up at the spectacular Annapolis Harbor. From there, it is only a short walk to the United States Naval Academy, which has called Annapolis home since 1850.
Saint Mary’s City, Maryland
Saint Mary’s City offers a unique view of Maryland’s past, with its downtown area centered around the historic site of the first English colonial settlement in 1634. This living history museum, akin to a smaller version of Colonial Williamsburg, features reconstructed buildings, costumed re-enactors, and interactive exhibits. With all the history in town, it is no wonder that the historic Saint Mary’s College of Maryland has one of the nation’s best archaeological field programs! Make sure you also visit the waterfront to enjoy the great views, as well as the replica 1634 sailing ship Maryland Dove.
Every small town along the Chesapeake Bay has its own story of tradition and transition. These communities have shifted over the centuries from colonial maritime ports to modern tourist destinations, yet have, by and large, done a great job of preserving their share of the region’s rich history and vibrant culture. Whether you prefer historic architecture, scenic waterfronts, or lively cultural events, these Chesapeake downtowns provide an inviting tapestry of experiences that showcase the best of Maryland and Virginia.
