6 Of The Most Charming Small Towns To Visit In The Mid-Atlantic
Not only is the Mid-Atlantic region of the United States an incredibly scenic part of the country, but it’s also one of the richest in terms of character and charm. Settled by Europeans in the 1600s, it was here in the many communities that sprung up in the years before the Revolutionary War that the seeds of independence were sown and where the country’s early history can be experienced.
For travelers looking to explore this beautiful part of the USA, these small towns - including Cape Charles and Chincoteague in Virginia, Shepherdstown in West Virginia, Bethany Beach in Delaware, along with Havre de Grace and Chestertown in Maryland - each provide a fun way to experience the best this region has to offer. For ideas and inspiration for your USA travel itinerary, read through this list of six of the most charming small towns to visit in the Mid-Atlantic region.
Cape Charles, Virginia
Its location at the southern tip of the Eastern Shore overlooking the Chesapeake Bay has earned Cape Charles a place on countless lists of the prettiest places to visit in the USA. Established in 1886 along with the railroad, much of the town’s best architecture has been preserved in the Cape Charles Historic District, including many buildings connected to its maritime and railway history. Notable examples include the Seafood Headquarters from 1886, Mitchell House from 1884, and the Palace Theatre built in 1941, to name but a few.
The Cape Charles Museum and Welcome Center, housed in a former power plant, is a good source of additional information about these buildings and the town’s history and development. Another of Cape Charles' top attractions is the Cape Charles Beachfront, which stretches along Bay Avenue and offers calm waters ideal for family swimming as well as pleasant sunset strolls. Other outdoor activities include exploring the 29-acre Cape Charles Natural Area Preserve with its coastal trails and views over the Chesapeake Bay.
Shepherdstown, West Virginia
Only a 90-minute drive from Washington DC, the West Virginian town of Shepherdstown makes for an excellent side trip for visitors to the nation’s capital. Founded in 1762, it holds the title of the oldest town in the state, so not surprisingly, some of the best attractions are located in Shepherdstown Historic District. Many of the most interesting buildings can be seen along German Street, the town’s main street, many built in Federal style in the late 1700s. Highlights include the Entler Hotel Museum, built in 1786 and home to the Historic Shepherdstown Museum with its exhibits about the town's role during the Civil War.
Other fun things to do in Shepherdstown include hiking or biking the trails along the Potomac River and the C&O Canal Towpath, joining a fun ghost tour of the town, or visiting during the Contemporary American Theater Festival hosted each summer by Shepherd University.
Havre de Grace, Maryland
Havre de Grace is located just off the I-95 between Baltimore and Wilmington and boasts a lovely scenic setting at the mouth of the Susquehanna River, where it meets the Chesapeake Bay. Named by French settlers as the "Harbor of Grace," there are plenty of fun things to do here, including visiting the Concord Point Lighthouse, the oldest lighthouse in continuous operation in Maryland, and strolling the Havre de Grace Promenade, a scenic boardwalk along the waterfront that’s also popular for fishing.
The promenade also leads to the Maritime Museum, which celebrates the area's rich nautical heritage, and the Havre de Grace Decoy Museum, showcasing the art of decoy carving that the region is famous for. More outdoor fun can be enjoyed at Susquehanna State Park, popular for its hiking, biking, and horseback riding trails. You can also pop into the Rock Run Historic Area with its old mill and mansion.
Chestertown, Maryland
Its lovely setting along the banks of the Chester River makes the town of Chestertown a must-visit destination in Maryland. Established in the 18th century, it’s to Chestertown Historic District that visitors should go first. This charming downtown area, with its cobblestone streets lined with buildings dating back to the colonial era, is home to great shopping experiences in its many art galleries and studios. It’s especially fun during the district’s First Friday events, when shops and galleries stay open late.
Chestertown Waterfront is another great place to explore, as well as embark on fun cruises along the Chester River. The town also hosts the annual Chestertown Tea Party Festival, commemorating the colonial defiance of 1774 with re-enactments and a celebratory tossing of tea into the river. Other attractions in Chesterton worth a visit include Eastern Neck National Wildlife Refuge, a sanctuary for migratory birds and native wildlife with hiking trails, kayaking, and bird watching; the Kent County Historical Society with its insights into Chestertown's past; and the Sultana, a schooner built in 1768 that offers hands-on experiences of 18th-century seafaring life.
Chincoteague, Virginia
Thanks to its island setting, Chincoteague is not only one of the most unique Mid-Atlantic small towns, it’s one of the prettiest. Located on the Virginia Eastern Shore and accessible by a bridge from the mainland, this peaceful island retreat serves as the gateway to the Assateague Island National Seashore, a protected area that offers pristine beaches, dunes, and marshes teeming with wildlife. The Chincoteague National Wildlife Refuge, part of Assateague, is especially popular for birdwatching with opportunities to see a variety of migratory birds.
It’s also here that the famous Chincoteague ponies roam freely, apart from during the annual Pony Swim when they're herded to Chincoteague Island. Part of the Fireman's Carnival, the event culminates in Pony Penning, where some are auctioned to help manage the herd size and raise funds for the local fire department. The Assateague Lighthouse is another popular reason to visit and boasts panoramic views of the surrounding area.
Bethany Beach, Delaware
Bethany Beach is a great spot to visit in Delaware for those wanting to spend time by the Atlantic Ocean. For these folks, strolling the town's promenade is a must. Lined with shops, eateries, and arcades, it’s the perfect spot to grab an ice cream and shop for souvenirs while soaking up those ocean views. Pack those bathing costumes, as the beach itself boasts wide, sandy shores perfect for sunbathing, castle building, and swimming, with lifeguards on duty during the summer months.
Bethany Beach also stands out for its cultural offerings, including the Bethany Beach Boardwalk Arts Festival held in September and the fun weekly summer concerts at the bandstand. For those seeking more adventure, the nearby Delaware Seashore State Park provides ample opportunities for hiking, fishing, and exploring the coastal marshes.
The Final Word
Whether you’re planning a day trip, a romantic weekend retreat, or even a weeklong family vacation, these Mid-Atlantic communities have lots to offer. From the soft sands of Bethany Beach and Cape Charles to Shepherdstown's historic streets and the old colonial architecture of Chesterton, with stops at Chincoteague and Havre de Grace along the way, these six most charming small towns to visit in the Mid-Atlantic are just waiting to be explored… so start packing!
