7 Most Laid-Back Small Towns In Chesapeake Bay
The shores of the long, narrow estuary known as Chesapeake Bay are lined with a collection of Maryland and Virginia towns that are ideal for those seeking a tranquil escape. The bay’s natural beauty and commercial heritage combine in these towns to create communities that are steeped in history and full of easy-going charm. Read on to discover why Saint Mary's City, Salisbury, Cambridge, Cape Charles, Chestertown, Urbanna, and Oxford are among the most laid-back small towns in the Chesapeake Bay.
Saint Mary’s City, Maryland
Established in 1634, Saint Mary’s City is the site of Maryland’s first permanent English settlement. A large portion of the old town serves as a living history museum of colonial life (similar to but smaller than Colonial Williamsburg), with restored 17th-century buildings and costumed interpreters. Historic preservation is a passion at the nearby Saint Mary’s College as well, which has a classic campus that is perfect for a contemplative stroll at a leisurely pace. Continue your walking tour at the beautiful bayfront, where you will find a replica 1634 sailing ship that now acts as a floating museum.
Salisbury, Maryland
With a population of 33,000 that makes it the “big city” of Maryland’s Eastern Shore and the entire Delmarva Peninsula, Salisbury deftly balances a small-town feel with urban conveniences. The downtown area is highly walkable, with quaint shops and charming eateries that really shine during the monthly “Third Friday” festival. The excellent Salisbury Zoo provides an informative diversion, and the scenic banks of the Wicomico River are ideal for a peaceful walk. For nature enthusiasts, the nearby Pemberton Historical Park offers tranquil trails through wetlands and forests, adding a touch of the wild to your visit.
Cambridge, Maryland
Cambridge, established as a colonial Maryland seaport in 1684, delights visitors with its historic downtown and beautiful waterfront. The heart of downtown Cambridge features lovingly preserved 19th-century buildings and a scenic walkway along the Choptank River. Be sure to visit the downtown museum dedicated to Harriet Tubman, who was born into slavery nearby, and delve into the area’s significant role in the Underground Railroad. As a thriving community of 13,000 with a laid-back pace but plenty to do, you will see why Cambridge often rates as one of the most livable small towns in America.
Cape Charles, Virginia
Set at the southern tip of Virginia’s slice of the Delmarva Peninsula, Cape Charles’ connection to the rest of the state changed with the completion of the Chesapeake Bay Bridge Tunnel in 1964. What has not changed, however, is the town’s relaxed coastal vibe, Victorian architecture, and beautiful beaches. Cape Charles’s historic district invites you to slow down and appreciate its quaint charm, while its sandy beaches are perfect for sunbathing, beachcombing, and watersports. And, if you enjoy fishing, the Cape Charles Fishing Pier is one of the premier spots for anglers in the entire Chesapeake Bay region.
Chestertown, Maryland
Chestertown is a Chesapeake Bay haven for those seeking a peaceful retreat amidst natural beauty and a fine collection of well-preserved Georgian and Federal-style buildings. Along with the great architecture, art lovers will appreciate the Kent Cultural Alliance and the various galleries that dot the town. Spend a leisurely afternoon exploring the waterfront, and check out the amazing replica of the 1768 schooner Sultana. Chestertown was the site of a Revolutionary-era “tea party” in 1774 and celebrates its maritime heritage each year with a fantastic Sultana Downrigging and Tall Ships Festival.
Urbanna, Virginia
For a few days each November, Urbanna sheds its status as a quiet village of 500 and welcomes tens of thousands of visitors for the annual Virginia Oyster Festival. If you love oysters but not big crowds, come any other time of year to experience a quaint and relaxed Urbanna. The town’s waterfront park provides a scenic spot to watch boats come and go, and the nearby Urbanna Creek is perfect for kayaking and paddleboarding. The friendly, small-town feel makes Urbanna a welcoming destination if you seek an alternative to everyday hustle and bustle.
Oxford, Maryland
Oxford, one of the oldest towns in Maryland, pairs historic elegance with a picturesque but working waterfront that still serves a fleet of fishing boats along with pleasure boats. The town’s narrow streets and well-preserved colonial structures, such as the Oxford Customs House, offer a glimpse into the past. Bring a piece of Oxford history to life by taking the Oxford-Bellevue Ferry, which has existed in various forms for nearly 350 years, to the neighboring (and similarly charming) town of Bellevue across the serene Tred Avon River. You may never want to head back home!
Once heavily polluted and scarred by industry, Chesapeake Bay is now a busy commercial waterway that has also recovered its status as one of the most beautiful natural features of the eastern United States. The small towns around the bay each offer their own unique charm and laid-back ambiance, providing a welcome respite from the hectic pace of modern life. So pack your bags, set your attitude to “chill,” and soak up the serene satisfaction of Chesapeake Bay’s most charming towns.
