Leesburg Historic District, By Strawser - Own work, CC BY-SA 3.0, File:7and15 Leesburg.JPG - Wikimedia Commons

9 Underappreciated Towns to Visit in Virginia

Virginia is an undoubted jewel of the Mid Atlantic United States, where fascinating history, picturesque natural beauty, and loads of authentic Americana can be found. Officially known as the “Commonwealth of Virginia,” the State is well known for its natural landmarks, including the Chesapeake Bay and the Blue Ridge Towns, while its historic colonial towns bring guests back to the days of the 18th and 19th centuries. For anyone looking for a special vacation destination, then Virginia and its welcoming towns should certainly not be overlooked. Here some of the very best of the USA can be found ready to create truly special memories for the solo traveller and family alike. So hit the road this travelling season, and come spend time in the beautiful Virginia, where history, nature, and small town charm come together in a most extraordinary way.


Downtown Onancock, Virginia.
Downtown Onancock, Virginia. Editorial credit: John Blottman / Shutterstock.com

One of Virginia’s oldest colonial settlements, the town of Onancock, was founded way back in the 1680s! A historic and quaint community with a modern population of just over 1,200 residents, Onancock is a great place to experience small-town life and get better acquainted with some of the nation’s earliest history in a beautiful natural setting. Situated on Virginia’s Eastern Shore, guests can take a most picturesque boat tour of the Chesapeake Bay with splendid views of the town, while a trip to the nearby Tobacco Island is a must for any nature lover. Enjoy such activities like sailing, swimming, cycling, and hiking in this most relaxing and raw island destination.

And of course, Onancock’s rich historic heritage can be appreciated by exploring its Historic District, which includes over 250 buildings and landmarks of historic importance. These include the Cokesbury Methodist Church (1854), the Ker Place Mansion (1799), and the Hopkins and Brother Store (1842) amongst others listed on the National Register of Historic Places. Add in a welcoming assortment of local restaurants, shops, and other businesses, and Onancock will surely leave any traveler with a most pleasant set of memories.


Downtown Leesburg, Virginia.
Downtown Leesburg, Virginia. Image credit: Wallygva via Wikimedia Commons.

Near the Potomac River and just some 32 miles from Washington, D.C., the historic town of Leesburg can trace its modern history to the 1750s. Seat of Loudoun County, a sizeable population of just under 49,000 residents call this inviting town home, where fascinating American history and a beautiful natural ambiance come together. Enjoy scenic views of the River and the eastern Blue Ridge Mountains, where outdoor activities like hiking, biking, and swimming are always popular. Meanwhile, Leesburg’s historic character can be fully appreciated in its Historic District, where many landmarks and buildings are included on the National Register of Historic Places. These include the Dodona Manor (1807), the Oatlands Plantation ({1804), and the Morven Park Estate (1780), amongst many others. Finally, guests of all ages can enjoy such fun cultural events like the Flower and Garden Festival and the Classic Car Show, that perfectly show off Americana and community spirit.

Cape Charles

The historic district in Cape Charles, Virginia
The historic district in Cape Charles, Virginia, via Robin Zeigler on IStock

Nestled within Chesapeake Bay on Virginia’s Eastern Shore, the town of Cape Charles is indeed a most charming and historic destination that no visitor to the State should miss. Established in the 1880s and now home to a population of just over 1,000 inhabitants, visitors to town can get a real sense of life in the late 19th century. Explore the inviting Historic District and marvel at several well-preserved buildings, homes, and cottages. Including the Mitchell House (1884) and the Mumford Bank (1895), amongst others listed on the National Register of Historic Places, Cape Charles’ intriguing past definitely comes alive here. Meanwhile the scenic allure of town makes it a wonderful place to enjoy a sojourn of a few days. Take in the Chesapeake Bay’s wondrous views, soak up the hot summer sun, spend the night at a most charming rental cottage, or go swimming, there is indeed always a delightful natural excursion to be had in Cape Charles. Add in a cute assortment of local businesses and restaurants, and this is one Virginia town that will surely leave one with the desire to return!


A lively street in downtown Farmville, Virginia.
A lively street in downtown Farmville, Virginia. By Puritan Nerd, CC BY-SA 4.0, Wikimedia Commons.

The seat of Prince Edward County, the town of Farmville, can trace its foundational roots to the late 1790s, where today, just over 7,000 people reside. Located just some 65 miles from Richmond (Virginia’s State Capital), this charming community is a cozy spot to enjoy a quieter pace of life. Enjoy the great outdoors in Farmville, with stops at such attractions as the High Bridge Trail State Park and Riverside Park. Here, fun activities like hiking, cycling, fishing, camping, and picnicking are popular and are ideal for the traveling family or solo guests alike. In addition, history-loving tourists can also appreciate Farmville, and time spent at the Historic District and the Sayler’s Creek Battlefield are great ways to get further acquainted with the nation’s past. At the latter, one can even witness exciting recreations of Civil War battles!

Finally as a small town, Farmville is charmingly full of welcoming local restaurants, shops and other businesses, while the early spring Heart of Virginia Festival has plenty of fun for all ages. From food vendors, live music, and a special firework show, this is one event that truly showcases the best of Americana.


Downtown Historic Staunton
Downtown Historic Staunton. Image credit MargJohnsonVA via Shutterstock

The town of Staunton can trace its colonial history back to the 1730s, and today it is considered an independent city (not within any State county). Home to a population of just over 25,500 residents, Staunton is beautifully located right in the Shenandoah Valley and guests will never find a shortage of beautiful natural surroundings and historic intrigue here. Spend time at several of the town’s inviting public parks, including Landes Park and Gypsy Hill Park, where relaxing afternoons and opportunities to go swimming, play tennis, golf, volleyball, skate, and biking are always popular.

Meanwhile, the history aficionado should not miss out on Staunton’s six historic districts, filled with a wide range of buildings and landmarks that span some 200 years of America’s past. Including the Sears House (1860) and the Oaks Mansion (1888), amongst many others listed on the National Register of Historic Places, Staunton’s historic charm makes it one of Virginia’s most fascinating places. Finally, do not forget about the Woodrow Wilson Presidential Library, which honors the nation’s 28th Commander in Chief, who was born in Staunton in 1856.

South Boston

South Boston Historic District via Wikipedia
South Boston Historic District via Wikipedia

Once known as Boyd’s Ferry, the historic town of South Boston was formally established in the 1790s and today it maintains a modest population of just over 7,500 residents. A nice place to discover America’s colonial past and enjoy some splendid outdoor ambiance, South Boston boasts mild winter and hot summer temperatures. Enjoy time at spots like the Reedy Creek Site, where excavations from prehistoric times remain continuously fascinating. Here, ancient burials, pottery, and other artifacts from the BC era make it one of Virginia’s most unique cultural attractions. Meanwhile, at the South Boston Historic District, guests can explore a number of landmarks on the National Register of Historic Places. These include the Fourqurean House (1830), the Berry Hill Plantation, and the E. L. Evans House (1892) amongst many others. Add in a fine assortment of local eateries and businesses in the downtown area, and South Boston truly is a fine slice of small-town America with loads of Virginia charm.


Main Street in Middleburg, Virginia
Main Street in Middleburg, Virginia. Editorial credit: Kosoff / Shutterstock.com

Middleburg was established in the 1780s, and today, this historic Loudoun County town is home to a humble population of just over 800 people. Also affectionately known as the “Horse and Hunt Capital” of America, Middleburg has been celebrated through the centuries for its role in developing foxhunting, horse racing, and large estate hunting grounds. Explore this charming community by spending an afternoon at the Historic District, where numerous landmarks bring guests back in time to the 18th and 19th centuries. Among the properties listed on the National Register of Historic Places include the Red Fox Inn and Tavern, which dates back to the 1720s and makes it the oldest continuously operating business in the country! Indeed a time machine like experience can definitely be felt in Middleburg, while a nice selection of cute souvenir stores, local diners, and other small businesses make it one Virginia locale that no visitor should miss.


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

A stunning place of natural beauty, the town of Woodstock is scenically located along the Shenandoah River and near the impressive Shenandoah National Park. Home to a population of just over 5,000 inhabitants, Woodstock can trace its colonial roots to the early 1760s and it maintains a wonderful historic character to it. Visit the Historic District and marvel at such landmarks as the County Courthouse (1790) and the Lantz Hall (1907) military academy building, amongst others that are listed on the National Register of Historic Places. Meanwhile, there is plenty of fun to be had near the River, and guests can enjoy peaceful walks and picturesque bike rides, all while enjoying warm summers and mild winters. Finally, Woodstock is also a great place to take in some of the best locally made Virginia wines, and an excursion to the North Mountain Vineyard and Winery surely cannot be missed!

Sugar Grove

View south along Virginia State Route 16 between Bonham Drive and Megan Lane in Sugar Grove, Smyth County, Virginia.
View south along Virginia State Route 16 between Bonham Drive and Megan Lane in Sugar Grove, Smyth County, Virginia. via Wikipedia. Source: Own work, Famartin. Wikipedia

A quiet and charming community of just over 600 inhabitants, Sugar Grove, is stunningly framed by both the Jefferson National Forest and the West Virginia Appalachian Mountains. Perfect for a road trip stopover, Sugar Grove stands as a picture-perfect snapshot of small-town USA, and guests can expect a most inviting array of local diners, shops, and businesses. Meanwhile for those looking to further be immersed in some of Virginia’s stunning local scenery, a day spent at the nearby Grayson Highlands State Park will surely not disappoint. Spanning an expansive area of some 4,500 acres, visitors can marvel at the wilderness or go camping, biking, hiking, and fishing in a most beautiful natural retreat. Indeed whether it's enjoying the outdoors or simply relaxing in the small-town ambiance, Sugar Grove is simply a nice little place that anyone in the southwestern corner of Virginia should not overlook.

Legally known as the “Commonwealth of Virginia”, this State in the Mid-Atlantic region is indeed one of the nation’s most beautiful and inviting places to discover. From intriguing colonial history to unique natural wonders like the Chesapeake Bay, Virginia and its towns are awesome destinations to spend a holiday and get better acquainted with the concept of Americana. Visit the historic streets of Staunton or take in the stunning coastal views at Cape Charles, which, along with other wonderfully striking Virginia towns, mostly definitely warrant an appreciation. Whether is one is travelling solo, with friends, or with family, experiencing small town Virginia is one Made in USA holiday that will surely create a most special set of wonderful, picturesque memories.

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