Aerial view of Chincoteague Island, Virginia.

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. 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, visiting Virginia and its inviting towns is an adventure the whole family can enjoy.

While major cities like Richmond still receive much attention, these other often overlooked places are part of why the state is such a special place. So take to the road and see the Commonwealth of Virginia across an exploration of these great towns!

Cape Charles

Coastal view of Cape Charles, Virginia.
Coastal view of Cape Charles, Virginia.

Beautifully situated within the Chesapeake Bay, Cape Charles is a charming and romantic destination, allowing guests to 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 to it. Visit the inviting historic district and its assortment of homes, cottages, and other landmarks from the late 1800s that give a sense of what a Virginia rail town was like. For example, the 1932 U.S. Post Office and 1884 Mitchell House stand out with their riveting tals.

Cape Charles is also a great place to enjoy being outdoors, and with its hot summers and mild winters, it always has a pleasant environment. Enjoy stunning views of the Chesapeake Bay, go swimming, rent a cabin, and even play a round of golf or two at any of the area’s premiere courses.


View of Middleburg, Virginia on the Fourth of July.
View of Middleburg, Virginia on the Fourth of July.

Just over 800 inhabitants call Middleburg home, 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, and famed steeplechase horse racing in the nation's early days. Today, guests can get a sense of living history when visiting this town, and the Middleburg Historic District is not to be missed. Listed in its entirety on the National Register of Historic Places.

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 establishments! Meanwhile, like any charming small American town, an assortment of excellent local eateries and shops populate much of the landscape. Namely, the Little Wonder Cafe and South China Cafe shine with great food, drinks, and ambience.


Historic buildings and stores along Market Street in Onancock, Virginia.
Historic buildings and stores along Market Street in Onancock, Virginia. Editorial credit: John Blottman /

Onancock, on the eastern side of Virginia, is one of the state’s oldest towns and one of the United States’ as well. With a colonial foundational history dating to the 1680s, the historic Onancock is indeed a most quaint and fascinating place to learn more about the past and enjoy beautiful natural surroundings. Spend time at the Historic District, where some 267 distinct buildings and landmarks can be found, all reflecting a diverse range of architectural designs from Federal to Late Victorian Styles.

Take a scenic boat tour on the Chesapeake Bay and enjoy town views, or take a day trip to the nearby Tobacco Island. Here, tourists can enjoy wonderful activities like swimming, sailing, and even kayaking in a wide-open space that is perfect for the solo traveler and traveling family alike.


Aerial view of historic buildings in Leesburg, Virginia.
Aerial view of historic buildings in Leesburg, Virginia.

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 inhabitants, the town has a bustling environment with a prime location. It lies near the Potomac River and just some 40 miles from the nation’s capital, Washington D.C. Parallel to this, the town is nestled at the base of the Eastern Blue Ridge Mountains, providing both urban and natural views to adore.

While natural charm is prominent, Leesburg shines with its cultural activities, such as the Flower and Garden Festival and the Leesburg Car Show, where community spirit is evident and many local vendors sell their best items. Meanwhile, Leesburg is well known in the region for its preserved historic district. Discover landmarks like the 1804 Oatlands Plantation, the 1872 Paxton Mansion, and the 1780 Morven Park Estate. Indeed, for a time machine-like experience to 18th and 19th-century America, visiting this side of Leesburg is one excursion that travelers will want to take advantage of.


The scenic Seven Bends State Park near Woodstock, Virginia.
The scenic Seven Bends State Park near Woodstock, Virginia.

Woodstock is a lovely mid-sized town with just over 5,000 inhabitants in Virginia. Located along the Shenandoah River and adjacent to the wondrous Shenandoah National Park, it is a great place to explore the outdoors. The Shenandoah National Park is less than an hour away and boasts 200,000 acres of pristine wilderness, perfect for outdoor drives, hikes, and camping. In addition, outdoor adventurists will not want to miss the Seven Bends State Park, which has incredible swimming, cycling, hiking, and wildlife-watching opportunities.

Back in town, Woodstock’s historic ambiance will satisfy those looking for a unique sampling of the past. Founded in 1761, Woodstock’s Historic District has several 18th, 19th, and early 20th-century landmarks, including the 1790 County Courthouse and 1909 Lantz Hall. And with hot summers and mild winters, there is never really a wrong time to enjoy all Woodstock offers, including a bevy of welcoming local restaurants and shops perfect for a weekend getaway.

South Boston

View of Paul C. Edmunds Park in South Boston, Virgina.
View of Paul C. Edmunds Park in South Boston, Virgina.

Known for its hot summer and mild winter temperatures, 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 boasts with over 8,000 residents, and it 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, which include the Berry Hill Plantation, the 1892 E.L. Evans House 1892, and the 1830 Fourqurean House, amongst others.

Or, for a unique experience, one can opt for the Reedy Creek Site to view modern excavation sites that reveal findings from the prehistory of America before colonial contact. Including pottery, ancient burials, and other remnants from the BC period, this is a fascinating and unique attraction.


A lively street in downtown Farmville, Virginia.
A lively street in downtown Farmville, Virginia. By Puritan Nerd - I took this photograph myself in Farmville., CC BY-SA 4.0, Wikimedia Commons.

Farmville is just some 65 miles from the Virginia State capital of Richmond and is a nice little spot to enjoy for a one or two-day trip. As the seat of Prince Edward County with just under 7,500 inhabitants, the town has a bustling vibe palpable upon arrival. Most people head straight for the outdoor attractions, and guests can spend time at the famous High Bridge Trail State Park. Here, raw nature is never far away, best experienced through activities like biking, hiking, camping, fishing, and old-fashioned picnicking.

Similarly, the charming ambiance of Riverside Park is always a delight. Meanwhile, as a historic town, tourists can discover sites such as the Farmville Historic District and the Sayler’s Creek Battlefield, complete with Civil War battle recreations! While these sites are open year-round, visitors in May can experience the Heart of Virginia Festival, where live entertainers, food vendors, and spectacular fireworks shows dazzle the young and old.

Sugar Grove

The Mount Rogers National Recreation Area near Sugar Grove, Virginia.
The Mount Rogers National Recreation Area near Sugar Grove, Virginia.

Just over 600 permanent residents call the community of Sugar Grove home, which the West Virginia Appalachian Mountains and the sprawling Jefferson National Forest beautifully surround. A charming snapshot of rural USA, visitors will find many welcoming local shops, family-owned eateries, farmer’s markets, and other quaint surroundings. To this end, many people find it a nice place to settle in after a busy holiday schedule.

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 the Grayson Highlands State Park, which boasts 4,500 acres of scenic wilderness. Or, opt for a stroll through the town center, where outlets like Hunt Brothers Pizza and The Farmhouse Market make for a relaxed and inviting afternoon full of small town charm.


Rustic buildings along the historic district in Staunton, Virginia.
Rustic buildings along the historic district in Staunton, Virginia. Editorial credit: MargJohnsonVA /

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, history lovers will surely not want to pass by this town with an impressive six historic districts! A veritable living museum, guests can explore over two centuries of America’s past with many 18th and 19th-century landmarks and museums in town.

These include the 1860 Sears House and the 1888 Oaks Mansion, which offer tours that transport one to a bygone era. In addition, the Woodrow Wilson Birth Home and Museum offers unique insights into the President’s early life and his consequential leadership during the First World War. Meanwhile, Staunton also boasts several inviting public park spaces that are great ways to enjoy being outside. 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.


Coastal view of Chincoteague, Virginia
Coastal view of Chincoteague, Virginia

Chincoteague, a town on Virginia’s Eastern Shore, including 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 natural wild pony population. 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. However, be sure to catch a sight of the famed Chincoteague Ponies, as their majestic grandeur makes a visit here worth the traveling.

In July, the annual Pony Swim delights excited crowds as ponies swim across the Assateague Channel from Assateague Island to Chincoteague in a special cultural event. Farm fairs and pony auctions follow, meaning the chance to purchase this special animal will make the kids in any traveling family very happy!

A vital component of the Southeastern and Mid-Atlantic United States, the “Commonwealth of Virginia” is a place of 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. From the island beauty of Chincoteague and its beloved ponies to the historic center of Middleburg and beyond, these charming and welcoming Virginia towns are incredible places of discovery for the entire family, young and old! Do not wait any longer; visit Virginia and its wealth of attractions, which are ready to welcome all with a thirst for a memorable vacation.

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