7 Towns In Chesapeake Bay With the Best Downtown Areas In 2024
Chesapeake Bay is the largest estuary in the United States, bordering the mid-Atlantic states of Maryland and Virginia and stretching from the Susquehanna River in the north to the Atlantic Ocean at Hampton Roads in the south. Dozens of waterfront towns sit along the bay’s winding shoreline, some of which have served as ports for more than 300 years. Chesapeake Bay is a perfect destination if you love historic downtowns, but its small towns also have plenty of modern amenities and entertainment options waiting for you in 2024.
Annapolis, Maryland
Annapolis may be Maryland’s capital city, but its compact size and population of only around 40,000 give it a small-town feel. Established in 1649 and the state capital since 1694, Annapolis has a fabulous colonial-era downtown with historic brick buildings running along narrow streets. The easy trek from the 1779 Maryland State House down to the waterfront passes local eateries like Chick & Ruth's Delly, boutiques like the Lucky Knot, and much more. Home to the U.S. Naval Academy since 1850 and located fewer than 35 miles from both Baltimore and Washington, DC, Annapolis is always buzzing with activity.
Williamsburg, Virginia
Williamsburg is famous as the home of Colonial Williamsburg, 300 acres of living history featuring costumed re-enactors and street after street of rebuilt or refurbished colonial-era buildings. While an admission fee is required to enter the buildings, walking the grounds is free. You can walk straight from Colonial Williamsburg into the remainder of town, founded in 1632 and featuring the nearby College of William and Mary, established in 1693. Adjacent to both the park and the college is Williamsburg's downtown shopping and entertainment district with more 40 shops and eateries, including local staples like Wythe Candies and national retailers such as Lululemon.
Cambridge, Maryland
Cambridge, home to about 13,000 residents, has been a port town on the Chesapeake for nearly 350 years. The town’s most famous figure, Harriet Tubman, was born into slavery, escaped to freedom, and risked her life as a leader of the Underground Railroad that guided other slaves to freedom. In addition to the museum honoring Tubman, downtown Cambridge includes several historical markers and local retailers like Black Water Bakery and Butterfly Boutique. Cambridge’s perfectly walkable downtown area is one of the reasons it has been rated one of the most livable small towns in America.
Urbanna, Virginia
If you want to experience Urbanna at its busiest and most energetic, come in late fall for the annual Urbanna Oyster Festival (November 1-2, 2024), which can pack up to 75,000 visitors into a town that usually has only 500 residents. Or, if you prefer things quieter and more laid-back, come pretty much any other time of year! A former tobacco port founded in 1680, Urbanna’s waterfront is perfect for pleasure boats, and its historic downtown is ideal for a day of walking, shopping, and dining or just a quick trip to pick up some fresh oysters at Walton’s or Shores & Ruark.
Chestertown, Maryland
Chestertown was founded in 1706, and in 1774 was the site of a “tea party” protest similar to the one in Boston. That event is re-enacted each year along the waterfront, which is also home to the Sultana, a spectacular reproduction of a 1768 sailing ship that serves as a floating museum. The annual Sultana Downrigging and Tall Ship Festival (November 1-3, 2024) is a grand celebration of Chestertown’s maritime heritage. The downtown area is full of historic buildings like the Prince Theatre (home to the Garfield Center for the Arts), and Chestertown’s Washington College (1782) is the oldest college founded after American independence. History is alive at every turn in Chestertown!
Cape Charles, Virginia
Cape Charles overlooks the mouth of Chesapeake Bay from its perch at the southern edge of the Delmarva Peninsula and also sits at the northern end of the 17-mile-long Chesapeake Bay Bridge and Tunnel that spans the bay’s mouth. Before the arrival of the bridge in 1964, Cape Charles was an important railroad and ferry terminal, and its compact downtown area boasts several well-preserved Victorian homes from that era. After checking out downtown Cape Charles hotspots like Shanty Seafood and Brown Dog Ice Cream, head to the town beach, charter a fishing boat, or head to nearby Eastern Shore National Wildlife Refuge or Kiptopeke State Park for hiking, birdwatching, and more.
Salisbury, Maryland
With a population of around 33,000, Salisbury is Maryland’s biggest town on its part of the Delmarva Peninsula, known as the Eastern Shore. Salisbury is a gateway to Maryland’s primary Atlantic beach town, Ocean City, as well as the nearby Delaware beaches. Yet the town is well worth more than just a quick stopover, as it has a nice downtown area with local shops like Karma's Closet and fun eateries like Roadie Joes. The Salisbury Zoo is also quite impressive for a small community. Salisbury’s monthly “Third Friday” festival continues year-round (outdoors from April through November) and offers a fine collection of live music, craft vendors, and fun for the whole family.
While still a busy and important commercial waterway, Chesapeake Bay has rebounded from its heavily polluted past and has become one of the premier vacation and recreation areas in the region. Towns that used to rely on fishing, ferries, or tobacco shipping now welcome visitors to their cozy downtowns with open arms. The communities that surround the Chesapeake Bay are full of history, charm, and family fun—so do not delay in making your 2024 travel plans!
