10 of the Most Overlooked Towns in Virginia
Admitted to the Union in 1788, the Commonwealth of Virginia is one of the most beautiful states in the Mid-Atlantic United States and a dream destination for travelers seeking charming small towns in Virginia. As the 12th most populous state with some 8.7 million residents, it boasts splendid natural beauty, fascinating history, and loads of American charm. Known for such attractions as the Blue Ridge Mountains and the Chesapeake Bay, its coastal villages, mountain hamlets, and historic main streets make visiting Virginia and its inviting towns an adventure the whole family can enjoy.
While major cities like Richmond still receive much attention, these other often overlooked places are part of what makes the state such a special place to road trip. From waterfront escapes to mountain getaways, the following Virginia small towns offer walkable historic districts, independent shops, and easy access to the outdoors. So take to the road and see the Commonwealth of Virginia through an exploration of these great towns!
Cape Charles
Beautifully situated on the Chesapeake Bay, Cape Charles is a charming and romantic coastal town where visitors can experience some of Virginia’s fascinating past. Home to a population of nearly 1,200 residents, the community was established in the 1880s on the state’s Eastern Shore, and today it continues to have a genuine 19th-century allure. Stroll the inviting historic district and its assortment of colorful homes, cottages, and landmarks from the late 1800s that reveal what a Virginia rail town was like. For example, the 1932 U.S. Post Office and 1884 Mitchell House stand out with their riveting tales.
Cape Charles is also a great place to enjoy the outdoors, and with its hot summers and mild winters, it offers an inviting climate most of the year. Enjoy stunning sunsets over the Chesapeake Bay, relax on the sandy public beach, go swimming or paddling, rent a cabin, and even play a round or two at one of the area’s premier golf courses. It is an easy pick for couples’ getaways and family-friendly Virginia beach weekends.
Middleburg
Just over 800 inhabitants call Middleburg home, a picturesque Northern Virginia town also known as the “Horse and Hunt Capital” of the United States. Established in 1787, Middleburg played a vital role in developing large estate lands, foxhunting traditions, and famed steeplechase horse racing in the nation's early days. Today, visitors can experience living history when exploring this walkable community, and the Middleburg Historic District—listed in its entirety on the National Register of Historic Places—is not to be missed, especially on a day trip from Washington, D.C.
Explore such places as the Red Fox Inn & Tavern, which, with a history dating back to the 1720s, is one of the country’s oldest continuously operating inns and a bucket-list stop for history lovers. Meanwhile, like any charming small American town, an assortment of excellent local eateries, wine-tasting rooms, and boutiques line the streets. Namely, the Little Wonder Cafe and South China Cafe shine with great food, drinks, and ambience, making Middleburg a standout small town getaway in Virginia’s horse country.
Onancock
Onancock, on Virginia’s Eastern Shore, is one of the state’s oldest towns and among the earliest settlements in the United States. With a colonial history dating to the 1680s, historic Onancock is a quaint and fascinating place to learn more about the past while enjoying beautiful natural surroundings along the Chesapeake Bay. Spend time in the Historic District, where some 267 distinct buildings and landmarks can be found, reflecting a diverse range of architectural designs from Federal to Late Victorian styles.
Take a scenic boat tour on the Chesapeake Bay and enjoy postcard-worthy views of the harbor, or take a day trip to nearby Tobacco Island for a quiet beach escape. Here, visitors can enjoy activities like swimming, sailing, bird-watching, and kayaking in a wide-open space that is perfect for both solo travelers and families planning a relaxed Eastern Shore vacation.
Leesburg
Leesburg was established in the 1740s and named for the prominent Lee family, which included General Robert E. Lee during the American Civil War. Home to a population of just under 50,000 residents, this Northern Virginia town has a bustling feel and a prime location. It lies near the Potomac River and only about 40 miles from the nation’s capital, Washington D.C. At the same time, Leesburg is nestled at the base of the Eastern Blue Ridge Mountains, providing both urban convenience and scenic mountain views.
While its natural charm is obvious, Leesburg really shines with its cultural activities, such as the Flower and Garden Festival and the Leesburg Car Show, where community spirit is evident and local vendors showcase their best items. Leesburg is also well known for its preserved historic district. Discover landmarks like the 1804 Oatlands Plantation, the 1872 Paxton Mansion, and the 1780 Morven Park Estate. For a time-machine-like experience to 18th- and 19th-century America, a weekend getaway to Leesburg is one excursion travelers from Washington, D.C. and beyond will not want to miss.
Woodstock
Woodstock is a lovely Shenandoah Valley town with just over 5,000 inhabitants in Virginia. Located along the Shenandoah River and within easy reach of the wondrous Shenandoah National Park, it is a great base for exploring the outdoors. Shenandoah National Park is less than an hour away and boasts about 200,000 acres of pristine wilderness, perfect for scenic drives, hikes, and camping. In addition, outdoor adventurists will not want to miss nearby Seven Bends State Park, which offers swimming, cycling, hiking, and wildlife-watching opportunities right on the river.
Back in town, Woodstock’s historic ambiance will satisfy travelers looking for a unique sampling of the past. Founded in 1761, Woodstock’s Historic District features several 18th-, 19th-, and early 20th-century landmarks, including the 1790 County Courthouse and 1909 Lantz Hall. With hot summers and mild winters, there is rarely a wrong time to enjoy all Woodstock offers, from welcoming local restaurants and breweries to independent shops that make this one of the most charming small towns in the Shenandoah Valley.
South Boston
Known for its hot summers and mild winters, the historic and charming town of South Boston (formerly known as Boyd’s Ferry) can trace its modern history to the 1790s. Today, it is the most populous town in Halifax County, with over 8,000 residents, yet it still maintains the ambiance of a welcoming American small town. Explore the beloved Historic District and several landmarks listed on the National Register of Historic Places, including Berry Hill Plantation, the 1892 E.L. Evans House, and the 1830 Fourqurean House, among others.
For a unique experience, head to the Reedy Creek Site, an archaeological area where excavations have revealed traces of life long before colonial contact. Pottery fragments, ancient burials, and other remnants from thousands of years ago make this a fascinating and educational attraction for visitors interested in Indigenous history and archaeology.
Farmville
Farmville is just about 65 miles from the Virginia capital of Richmond and is a great spot to enjoy on a one- or two-day trip. As the seat of Prince Edward County with just under 7,500 inhabitants, this college town has a bustling vibe that’s palpable upon arrival. Many visitors head straight for the outdoor attractions, especially the famous High Bridge Trail State Park. Here, raw nature is never far away and is best experienced through activities like biking, hiking, camping, fishing, and old-fashioned picnicking with views over the Appomattox River.
Similarly, the charming ambiance of Riverside Park is always a delight for travelers seeking green space near downtown. As a historic town, Farmville also offers sites such as the Farmville Historic District and nearby Sayler’s Creek Battlefield, sometimes complete with Civil War battle recreations. While these attractions are open year-round, visitors in May can experience the Heart of Virginia Festival, where live entertainers, food vendors, and spectacular fireworks shows dazzle both young and old.
Sugar Grove
Just over 600 permanent residents call the community of Sugar Grove home, a quiet corner of southwestern Virginia surrounded by the Appalachian Mountains and the sprawling George Washington and Jefferson National Forests. A charming snapshot of rural USA, visitors will find welcoming local shops, family-owned eateries, farmers’ markets, and other quaint surroundings. Many people find it a peaceful place to slow down and settle in after a busy holiday schedule or city stay.
Between the warm community spirit and the delightful natural ambiance, this is undoubtedly one Virginia locale that should not be overlooked. Enjoy biking, hiking, camping, and fishing at nearby Grayson Highlands State Park, which boasts thousands of acres of scenic high-country wilderness. Or opt for a stroll through the town center, where spots like Hunt Brothers Pizza and The Farmhouse Market make for a relaxed and inviting afternoon full of small-town charm.
Staunton
Staunton, famed as the birthplace of America’s 28th President, Woodrow Wilson, is full of historical stories dating back to its settlement in the 1730s. Located in the heart of the Shenandoah Valley, this vibrant small city is a must-visit for history lovers, with an impressive six historic districts. A veritable living museum, Staunton invites guests to explore over two centuries of America’s past through its many 18th- and 19th-century landmarks and museums.
Highlights include the 1860 Sears House and the 1888 Oaks Mansion, which offer tours that transport visitors to a bygone era. In addition, the Woodrow Wilson Birth Home and Museum provides unique insights into the president’s early life and his consequential leadership during the First World War. Staunton also boasts several inviting public park spaces that make it easy to enjoy the outdoors. From Gypsy Hill Park to Landes Park, a delightful afternoon awaits all who wish to take in the natural sights of this historically charming town.
Chincoteague
Chincoteague, a town on Virginia’s Eastern Shore that includes the Island of Chincoteague, is one of the most scenic and beautiful places in the entire state. With a population of just under 3,000 residents, Chincoteague is widely celebrated for its stunning seaside vistas and wild pony population, protected nearby on Assateague Island. With numerous campgrounds, beach areas, charming bed-and-breakfast establishments, and fun boat tours, visiting Chincoteague is an excursion that all ages can truly relish. Be sure to catch sight of the famed Chincoteague Ponies, as their majestic grandeur alone makes the journey worthwhile.
In July, the annual Pony Swim delights excited crowds as ponies swim across the Assateague Channel from Assateague Island to Chincoteague in a beloved cultural event. Farm fairs and pony auctions follow, offering the chance to see these animals up close and celebrate a tradition that has defined this Virginia beach town for generations—an unforgettable highlight for many families.
A vital component of the Southeastern and Mid-Atlantic United States, the “Commonwealth of Virginia” is a place of both cultural and natural beauty. A historic center of early colonial America, Virginia’s fascinating past is only rivaled by its extensive natural allure, which includes the famed Chesapeake Bay and the scenic Blue Ridge Mountains. From the island beauty of Chincoteague and its beloved ponies to the historic streets of Middleburg and beyond, these charming and welcoming Virginia towns rank among the best small towns in the state for discovery. Whether you are planning a weekend getaway, a family vacation, or a longer road trip, Virginia’s towns are ready to welcome all who crave a memorable escape.
