Tourists taste local wine specialties at WineFest, St. Michaels, Maryland. Image credit tokar via Shutterstock

14 Most Beautiful Small Towns In Chesapeake Bay You Should Visit

The Chesapeake Bay towns of Maryland and Virginia offer a glimpse into early American history alongside present-day charm. With the oldest settlements dating back to the early 17th century, these small communities once served as important ports and continue celebrating their maritime roots. For instance, also referred to as the “pearl of the Chesapeake,” Rock Hall is known for its rich history of folk music and continues hosting numerous festivals celebrating regional culture and heritage.

Today, visitors can stroll through preserved colonial buildings and learn about regional industries like crabbing and oystering at the museum. There’s also the option to simply relax along the picturesque waterfront promenade while taking in scenic views of the renowned Chesapeake Bay. Each town, from bustling working ports to arts communities, shares a laid-back appeal perfect for day trips or longer visits throughout the year.

Urbanna, Virginia

Urbanna Virginia historical district, seen from Cross Street
Downtown Urbanna, Virginia Historical District. Image credit Mojo Hand, CC BY-SA 4.0, via Wikimedia Commons

A nautical adventure is up for discovery at the Urbanna Town Marina, where boating enthusiasts can enjoy a range of water activities, including sailing and fishing, against the backdrop of the river's tranquil waters. Relish the opportunity for a beach trip with the nearby Wake Beach and Yorktown Beach. What makes this Rappahannock River town even more special is its annual Urbanna Oyster Festival, a two-day event featuring parades, arts and crafts, and a bounty of fresh oysters.

Oxford, Maryland

The Robert Morris Inn in Oxford, Maryland.
The Robert Morris Inn in Oxford, Maryland. Image credit JE Dean via Shutterstock

Picture a tranquil haven on the Tred Avon River shores, and you will find yourself in Oxford, Maryland. To begin with, there is the intriguing Oxford-Bellevue Ferry, one of the nation's oldest privately operated ferries, still plying the waters since the late 1600s. You also have the chance to embark on a sail on the historic Skipjack Nathan of Dorchester out of Cambridge, a traditional wooden sailing vessel that offers tours of the surrounding waterways and the town's nautical traditions. Treat yourself to local cuisine at the renowned Robert Morris Inn, a historic establishment where you can enjoy a delectable feast overlooking the water.

St. Mary’s City, Maryland

Colonial ship at St. John's Site Museum at Historic St. Mary's City, Maryland.
Colonial ship at St. John's Site Museum at Historic St. Mary's City, Maryland. Image credit Regine Poirier via

It would feel like stepping into the living history when you enter the thresholds of the birthplace of Maryland, St. Mary's City. There is no better way to begin your discovery than to check out Historic St. Mary's City, an open-air living history museum, where costumed interpreters bring the town's 17th-century origins to life through engaging demonstrations and reenactments of daily colonial life. Stroll through the town, where well-preserved landmarks such as the Brick Chapel and the Maryland Dove showcase the town's significant role in the birth of religious freedom in the New World. Even the natural wonders of this historic destination are not behind, where the fascinating Woodland Indian Hamlet provides a serene setting for contemplation and relaxation.

Cape Charles, Virginia

Aerial View of Beach Homes in Cape Charles Virginia
Beach Homes in Cape Charles, Virginia.

Cape Charles has got your back if you are after endless pristine beaches, quaint small-town appeal, and abundant outdoor activities. You can and should unwind on the soft sands of Cape Charles Beach, basking in the warm sun and relishing the panoramic views of the Chesapeake Bay Bridge Tunnel, a marvel of engineering that spans the bay. Also, the gentle waves and golden sands create the perfect backdrop for sunbathing and water sports, including kayaking and paddleboarding. Add the Kiptopeke State Park to your list for an out-of-this-world experience, where remnants of a World War II concrete ship serve as an artificial reef, creating an underwater wonderland for divers and snorkelers to explore.

Chestertown, Maryland

Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland
Overlooking Chestertown, Maryland.

Along the verdant banks of the Chester River, Chestertown exudes a timeless charm that harks back to its colonial roots, ranking it among the US's favorites. Make a stop at Washington College's River and Field Campus, where the diverse ecosystems of the Eastern Shore come to life through educational programs and nature walks. The hidden gem of the Garfield Center for the Arts, a cultural hub hosting an array of theatrical performances and live music, offers an experience that encapsulates Chestertown's artistic flair. You must make time for the sprawling Washington College campus, where the renowned Miller Library houses a collection of rare manuscripts and historical artifacts, for a glimpse into the town's intellectual heritage.

Salisbury, Maryland

Beach promenade at Salisbury, Maryland.
Beach promenade at Salisbury, Maryland. Image credit travelview via Sephora

Salisbury, located on Maryland's Eastern Shore, boasts a population of 33,196 residents. It rests close to the Delaware border on the Delmarva Peninsula, just between the Chesapeake Bay and the Atlantic Ocean. Thanks to its strategic location, Salisbury functions as a key access point to Ocean City and Maryland's array of beachfront destinations. However, Salisbury has much more to offer within its own borders, attracting visitors with attractions like the Salisbury Zoo and the monthly "Third Friday" festival held in the downtown area. Beyond the summer influx of tourists, the presence of Salisbury University, a public institution established in 1925, significantly contributes to the town's economic and cultural vibrancy.

Irvington, Virginia

Street view in Irvington, Virginia
Street view in Irvington, Virginia.

It has been said that Virginia is for Lovers, and the town of Irvington, in particular, incorporates a parcel to cherish. This friendly town of almost 500 inhabitants is a fundamental portion of Americana and was named one of Coastal Living Magazine's 20 Best Coastal Places to Live in 2020, and it's simple to see why. White picket fences and surging sails proliferate in Irvington on the Rappahannock River. Onlookers can observe the yearly Turkey Shoot Regatta cruise from the shoreline for an energizing evening. Home to one of the most excellent cruising schools on the East Coast, Irvington is the ideal place to master the ropes.

Onancock, Virginia

Early evening street scene down Market Street, Onancock, Virginia.
Market Street, Onancock, Virginia. Image credit John Blottman via Shutterstock

Tucked between the Chesapeake Bay and the Atlantic Ocean, Onancock was called "the Gem of the Eastern Shore'' by Captain John Smith, the popular English pioneer in the 1600s. Nowadays, this dynamic town of 1,151 is chock-full of attractions and more than holds its claim against the other sections on this list. Adventure awaits on Onancock Creek by kayak up to a nearby vineyard, leading towards the island of Tangier from the town’s harbor.

Rock Hall, Maryland

Sitting by the waterfront in Rock Hall, Maryland.
Sitting by the waterfront in Rock Hall, Maryland.

The languid town that started on the shores of the Chesapeake has ended up a boater's haven since its establishment. Found at the mouth of the Chester River, this town of 1,198 individuals offers more than ten marinas, a yacht club, and world-class cruising. The Shore Stop is where travelers can discover the little but wonderful shoreline for dazzling views of the cove at nightfall. The Black Duck Inn has gorgeous rooms on the Marina, and visitors can grab a dessert later at Durdings Store. Rock Hall has the unmistakable air of an angling town. To learn more, free up some time to discover the Waterman Museum and dive into the town's history with free admission.

St. Michaels, Maryland

Part of St. Michaels Harbor in historic Saint Michaels, Maryland, in spring
St. Michaels Harbor in historic Saint Michaels, Maryland.

Maryland is known for its juicy fish, and the gorgeous town of St. Michaels is a fabulous place to undertake it. The Maryland blue crab is famous for its scrumptious meat, and it would be difficult to discover an eatery in town where this shellfish is not on the menu. On the off chance that clams are favored, you can make a shellfish collecting visit and get elbow-deep in a centuries-old convention on the Eastern Shore. Sail Selina II comes highly recommended in St. Michaels and may be a superb way to spend an evening. The company offers travels out into the narrows on a ravishing mahogany Thundering 20s period boat. Only a brief drive from St. Michaels, Tilghman Island is a little island that calls guests for some of the best views of the Bay.

Easton, Maryland

Thompson Park and the historic City center of Easton, Maryland.
Thompson Park and the historic City center of Easton, Maryland. Image credit grandbrothers via Shutterstock

Easton, also known as "the 8th Best Small Town in America," has a downtown zone with walkways, trees, and a unique Victorian-style design. As you wander through the historic district of Easton, the allure of its colonial architecture transports you to a bygone era. History buffs will find solace in the Avalon Theatre, a restored Art Deco gem hosting a vibrant array of performances, from live music to theater. Stroll through the Talbot Historical Society Museum, where the rich maritime heritage of the Chesapeake Bay comes alive through exhibits on shipbuilding and oystering. A visit to Pickering Creek Audubon Center has to be on your list. It offers serene trails that wind through lush wetlands and wooded areas, a haven for birdwatchers and hikers alike.

Havre De Grace, Maryland

Concord Point Light in Havre de Grace, Maryland.
Concord Point Light in Havre de Grace, Maryland.

Gazing over the serene waters of the Susquehanna River, Havre De Grace emanates a magnetic allure. Embark on a journey through maritime history at the Concord Point Lighthouse, a historic gem dating back to 1827 and standing proudly as a sentinel to the town's rich seafaring past. The Susquehanna Museum at the Lock House is all about a nature-infused adventure, offering a glimpse into the historic canal system and the intricate role it played in shaping the region's development. Another popular attraction is the Havre De Grace Maritime Museum, where exhibits bring the stories of the bay, its watermen, and their traditions vividly to life.

Stevensville, Maryland

View north along Maryland State Route 835C (Old Love Point Road) at Cockey Lane and East Main Street in Stevensville, Queen Anne's County, Maryland
East Main Street in Stevensville, Maryland. Image credit Famartin, CC BY-SA 4.0, via Wikimedia Commons

The charming town of Stevensville welcomes visitors with its pristine landscapes and panoramic vistas situated on Kent Island. You can discover the island's rich past at the Stevensville Train Depot Museum, which houses a fascinating collection of artifacts and antique locomotives that detail the island's pivotal role in developing the nation's railway system. Experience the island's natural wonders at Terrapin Nature Park, where meandering trails lead to picturesque beaches and serene wetlands, an ideal setting for birdwatching and nature photography. A drive along the Chesapeake Country Scenic Byway is among the highlights, soaking in the breathtaking landscapes and stopping by the island's hidden gems, such as the charming Kent Narrows, a bustling waterway brimming with maritime activities and quaint waterfront shops.

Chesapeake City, Maryland

View of Chesapeake City from the Chesapeake City Bridge, Maryland.
Chesapeake City from the Chesapeake City Bridge, Maryland.

Chesapeake City weaves its charm with a vibrant waterfront ambiance.  A taste of Chesapeake's maritime heritage is in full flavor aboard Chesapeake City Water Tours for a scenic journey along the canal. The Chesapeake City Bridge is a sight to behold, especially when a massive cargo ship passes beneath it – a truly unique experience. Another place to go to is Schaefer's Canal House, a historic restaurant where seafaring tales come to life, and don't miss the chance to enjoy their famous crab cakes.

Visiting any of these historic small towns along the Chesapeake Bay is sure to be a memorable experience. You will get a true sense of what life was like centuries ago as you walk through preserved colonial buildings and landscapes. Yet each town also has a vibrant culture and community today, whether it is through festivals, art scenes, working waterfronts, or college environments. Taking the time to slow down and explore one or more of these picturesque coastal gems will allow you to appreciate the natural beauty of the Chesapeake Bay while learning about the culture and heritage that helped shape this special region. The warm hospitality will make you feel part of the community and want to come back time and time again to these small towns with big charm.

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