TRAVEL GUIDE
The Best Small Towns in the Mid-Atlantic
These small towns are among the most charming in the Mid-Atlantic
The Best Small Towns in the Mid-Atlantic
There's something truly magical about small towns. Nestled along winding country roads, these humble destinations offer a retreat from the fast-paced modern world.
But what exactly defines a small town? According to the U.S. Census Bureau, a small town is typically a community with a population of less than 5,000 people. These quaint enclaves can be found all across America, each one exuding its unique charm and character.
Far from the bustling urban centers, these towns showcase the essence of simplicity, close-knit community, and a deeper connection with nature.
Whether you're seeking a quiet weekend getaway, a place to set down roots, or simply a change of scenery, small towns have a way of capturing hearts.
We hope you will join us as we explore the hidden gems nestled throughout the Mid-Atlantic, where small-town living is celebrated.
VIRGINIA’S NORTHERN NECK
Irvington, Virginia
Established in the late 1800s, Irvington, Virginia, is a charming small town located in the heart of Virginia’s Northern Neck. Originally named Carters Creek in honor of John Carter Sr., the son of Robert “King” Carter — the original land agent for the Northern Neck Proprietary of Lord Thomas Fairfax, Irvington, Virginia was then renamed in honor of Captain Levin Irvington. Today, Irvington, Virginia is a popular destination for visitors seeking a taste of small-town life on the Chesapeake Bay. Named to the National Register of Historic Places in the year 2000, Irvington, Virginia retains much of its historic charm, with many of the original homes still standing as well as a variety of local restaurants, including the popular seafood restaurant Dredge.
VIRGINIA HUNT COUNTRY
Middleburg, Virginia
Established in 1787 by Revolutionary War officer Level Powell, Middleburg, Virginia stands as one of the Mid-Atlantic’s most desirable destinations. Located midway between Alexandria, Virginia and Winchester, Virginia, Middleburg, Virginia — formerly known as Chinn’s Crossing — features some of the finest rural landscapes and country homes in the United States. Home to the National Sporting Library, an art gallery, museum, and research center for horse and field sports, Middleburg, Virginia is the geographic epicenter of Virginia Hunt Country.
VIRGINIA’S PIEDMONT
Sperryville, Virginia
Located on the foothills of the Blue Ridge Mountains in the heart of Virginia’s Shenandoah Valley, Sperryville, Virginia stands as one of the finest small towns in the Mid-Atlantic. Established in 1820 by Francis Thornton, the land that comprises Sperryville, Virginia is among the original area known as the Northern Neck Proprietary originally granted to Thomas Fairfax VI by King George II of Great Britain. Named to the National Register of Historic Places, Sperryville, Virginia stands as one of the Mid-Atlantic’s most prized destinations. With convenient access to the famous Appalachian Trail via popular routes such as Thornton Gap and Old Rag, Sperryville, Virginia is also regarded for its rich culinary heritage, which include fine restaurants such as Three Blacksmiths and acclaimed farmhouse breweries and distilleries such as Pen Druid Brewing and Copper Fox Distillery.
VIRGINIA’S PIEDMONT
Washington, Virginia
Washington, Virginia is a small town located in Rappahannock County, Virginia. Founded in 1796, it was originally known as Gay Street after the surveyor who laid out the town, John Gayle. It was later renamed in honor of the first president of the United States, George Washington. Today, Washington, Virginia is a charming historic town known for its picturesque views and quaint shops. Visitors can take a walking tour of the town to see its many historic buildings and landmarks, including The Inn at Little Washington, a five-star hotel and restaurant.
MARYLAND’S EASTERN SHORE
Saint Michaels, Maryland
Located along the Miles River in western Talbot County, Maryland, the historic town of Saint Michaels, Maryland is among the Mid-Atlantic’s most iconic destinations and among the many gems of Maryland’s Eastern Shore. Since its fouding, Saint Michaels, Maryland’s primary industry has been shipbuilding, with its primary export being a fast schooner style boat known as the Baltimore clipper. During the War of 1812, Saint Michaels, Maryland earned the reputation as “the town that fooled the British” for its clever strategy to evade incoming fire from the invading British forces. Today, Saint Michaels, Maryland is enjoying a renaissance with considerable restoration and rehabilitation of historic buildings in its central town square, and continues to serve as one of the most desirable destinations in the entire Mid-Atlantic region as a result of its enviable location along the Chesapeake Bay.
VIRGINIA WINE COUNTRY
Keswick, Virginia
Established in 1849, Keswick, Virginia stands as one of the Mid-Atlantic’s most charming small towns. Located moments from downtown Charlottesville, Virginia, the village of Keswick, Virginia is comprised of large farm estates, stunning mountain views, and winding country roads which have been cited as some of the most scenic in America.
THE RAPPAHANNOCK RIVER COMPANY
Create Your Next Home in the Mid-Atlantic
With our premium concierge service, it’s never been easier to create the home of your dreams.