Lexington, Virginia.

11 Cutest Small Towns In Virginia

Perhaps the most historical state in America, Virginia comes with many small towns of big personalities. Shining brightly with their own historical escapade and set within some of the most mesmerizing scenery of the country, these 11 towns are also the cutest in the state of Virginia.  


Waterfront in Chincoteague, Virginia.

The small island town on the Eastern shores of Virginia is known for its quintessential living on an island experience and the wild ponies in their natural environment near the Chincoteague National Wildlife Refuge. The quaint fishing community was made famous by Marguerite Henry's children's book Misty of Chincoteague and namesake film in 1961 focused on Chincoteague's wild ponies at the neighboring Assateague Island. The Museum of Chincoteague explains the history behind the wild horses while detailing other aspects of the region. The beach offers a relaxing day spent frolicking in the waters and basking in the sun, while the Assateague Lighthouse on the adjacent Assateague Island is a must-visit, offering the best views of the area from the top. The boutique shops and small dining establishments with a community-bound feel, including the nationally recognized for its frozen treats - Island Creamery, will diversify one's pastime. The NANA Wallops Island Flight Facility Visitor Center, inclusive with a free museum, exhibits information about NASA rocket programs and missions. 


The White Mill in Abingdon, Virginia.

Established by Daniel Boone in the 1770s, Abingdon is back-dropped by Western Virginia's gorgeous Blue Ridge Mountains for a perfect mix of outdoors and history. Part of the Rails-to-Trails route extending for 34 miles, the trailhead of the Virginia Creeper Trail is right in the middle of the town. Named for the steam engine that used to "creep" up into the Iron Mountains, it is perfect for hiking, biking, or horseback riding through the scenic surroundings. The cute restaurants in town serve dishes of locally sourced products, while the cobblestone sidewalks of the Historic District's stretching for 20 square blocks are lined with cultural and historical architecture from the 18th century. The art fanatics will love catching a play at the Barter Theatre and perusing the galleries at the William King Museum of Art. The restored 1870 railroad station comprises an eclectic Arts Depot. The historians will appreciate the Fields-Penn 1860 House Museum displaying the early 19th-century life in the region, while the elegant Martha Washington Inn & Spa from 1832 is a designated Historic Hotel of America.


Originally the town was named Guest Station after the explorer and surveyor Christopher Gist, who inscribed his experience of setting camp in the area with his son. The new name Coeburn is a collaboration from W. W. Coe, who was the Chief Engineer of the N&W Railroad, and Judge W. E. Burns, acquired by the town in 1894. The small town with an area of 2.0 square miles (5.3 km2) is a perfect base for those who want to explore the great outdoors of the state. Set on the Guest River, Coeburn is known for the many camping opportunities at the nearby Bark Camp Lake in the Jefferson National Forest, where one can also fish and go boating. The hikers and bikers will enjoy the Guest River Gorge Trail along the river on the former Interstate Railroad. The High Knob Lake Trail and the Little Stony National Recreation Trail are also popular among hikers for scenic strolls. The downtown is a charming and artistic spot with antique lamp fixtures along the streets and pedestrian bridges and brick sidewalks leading to local restaurants. The art galleries reveal why the town is part of the Lonesome Pine Artisan Trail, while the historic Lays Building offers a musical and relaxing environment where one can hear the melodies that celebrate the Appalachian region. 


Culpeper, virginia
A street in Culpeper, Virginia. Editorial credit: refrina / Shutterstock.com

Less than an hour from Fredericksburg, Charlottesville, and Washington DC, the small town of Culpeper is easily accessible via train, with a station right amid the historic downtown district. The Virginia Main Street program revitalized the town's Main Street for a perfect afternoon spent shopping at the local stores. The historic downtown district is dotted with Victorian and colonial homes, galleries, more shops, and restaurants. There are also the Culpeper History museum, historic homes, churches, and a horse show at Commonwealth Park. Originally surveyed by the young George Washington and later occupied by the pro-Independents during the Revolutionary War, the town is a perfect weekend getaway for the history buffs with plenty of beds and breakfasts to stay in-between exploration and discovery. The Old House Vineyards and the Belmont Farms Distillery offer samplings of local crafts, while Moonshine is also made legal at Belmont. 


Damascus virginia
Backbone Rock in Damascus, Virginia.

The mountainous Damascus is a hiker's dream come true, with the Appalachian Trail, the US Bicycle Route 76, the Iron Mountain Trail, and the Virginia Creeper Trail converging right in town. There is also the Virginia Birding Trail to stroll and the Mount Rogers Scenic Byway for a beautiful drive with vistas. Over one-thousand bicycles are rented each year in the "Trail Town USA," while the Blue Ridge Mountains, together with the nearby Mount Rogers National Recreation Area, contains the highest peak in Virginia. The fame to claim is celebrated through the Trail Day Festival in May, as the country's largest festival for the Appalachian hikers, with 30-some thousand hikers filling the area trails each year. Full of rustic beauty, the natural surroundings of Damascus will attest to other outdoor pursuits, enticing bikers, or kayakers on the river. The Mojoe's Trailside Cafe and Coffee house is a popular gathering spot following the active adventures. The cute town comes complete with a laid-back environment, chatty locals, and a relaxing atmosphere of the restaurants where one can truly let go over a shared meal. 


Virginia Military Institute in Lexington Virginia
Virginia Military Institute in Lexington, Virginia.

Honoring military history, Lexington was named after the namesake town in Massachusetts, where the first shot was fired in the American Revolution. Containing the burial grounds of the confederate generals Robert E Lee and "Stonewall" Jackson, along with historical sites and monuments, Lexington is home to the Virginia Military Institute and Washington and Lee University. Brimming with other historic sites and museums at every corner, the beautiful historic downtown listed in the National Register of Historic Districts will entice anyone. The cute town has much more to offer for non-war fanatics, such as lovely farm-to-table restaurants and the beauty of the Shenandoah Valley. There is a variety of specialty shops, boutiques, art galleries, and local cafes to diversify one's time spent. One can either stroll through or take a carriage ride around the town. The outdoorsy types will revel to hike the Laurel Run Trail, climb the Devil's Marbleyard with boulders, and bike the Goshen Pass.  


Originally a port town, the seaside and charming Onancock is set on the eastern shore as one of the oldest towns in Virginia for a relaxing getaway and a knowledge-filled experience. To get acquainted with the town's history, one must visit Ker Place and the Waterman's Museum, followed by a stroll through the neighborhoods filled with Victorian homes. Known for an artful flare, the town is best explored by foot with boutique shops and art galleries lining the streets, music and visual arts throughout, and live theater at the restored Roseland Theatre. Following a kayaking or canoeing trip through the local waters, there are three waterfronts brimming with restaurants for a scenic meal with a stunning eastern shore sunset. There are also many quaint shops and a cinema, while for diversified vistas, there is the nearby Tanger Island accessible by a ferry departure from town.


Staunton, Virginia
Historic district of Staunton, Virginia. Editorial credit: jack looney photography / Shutterstock.com

Set in the Shenandoah Valley, Staunton is a true eye-candy of a town, brimming with history, architecture, and culture. The American Shakespeare Center is the world's only authentic replica of the Blackfriars Theater, while the Frontier Culture Museum of Virginia is a living museum exploring the lives of thousands of colonial immigrants in America. There is a great choice of restaurants, shops, and cafes to visit between the Victorian architecture, all back-dropped by the fantastic mountains vistas. Known as Virginia's best-kept secret, the lovely town was first settled in 1732, acting as a state's capital at one point and birthplace of President Woodrow Wilson, whose house was built in 1846 atop the historic Gospel Hill. One can tour the seven galleries outlining Wilson's early years through the First World War. There is also the impressive Trinity Church with its own Tiffany window to marvel at. 


The tiny town of only 0.7 km² of land and some 200 residents was occupied by the namesake native tribe of the Algonquian people that resided in the area centuries ago. Set on charming Virginia's eastern shore, Wachapreague is known for its special character, beach fun, and some of the most pristine wetlands along the mid-Atlantic region. A popular base for fishers, the Wachapreague Channel winds from the town out to the barrier islands, passing through the seaside marsh. Avid boaters love to paddle where it eventually flows into the Atlantic Ocean in-between Cedar and Parramore Islands, a spot plentiful in game marlin or tuna. The eco-friendly, wrapped in Victorian-era aesthetics, welcomes tourists on eco-tours, with bird migration in the spring and fall when kayakers can also tour through the local waters. 


Lynchburg, Virginia, USA downtown from Monument Terrace at dawn.
Lynchburg, Virginia, downtown from Monument Terrace at dawn.

Lynchburg, a cute town for history fanatics, hosts historical sites like the Point of Honor, the Old Court House and Lynchburg Museum, Patrick Henry's Red Hill, the National D-Day Memorial, and the Appomattox Court House National Historical Park. Thomas Jefferson's Poplar Forest and personal retreat contain marvelous historical architecture. For everyone else, there are great coffee shops to relax and absorb the true sense of a quaint town living in Virginia. Set on the James River and back-dropped by the gorgeous Blue Ridge Mountains, the outdoor experiences with scenic views are endless and phenomenal for nature-bound pursuits, such as walking, hiking, and biking along the river trail, as well as over 40 miles of urban trails. Culture fans will appreciate the bluegrass and music festivals at the local parks and check out the historic Craddock Terry Hote old shoe factory turned into a boutique hotel. The town, oozing in southern charm, is full of character and history, with five districts on the National Register of Historic Districts.


Warrenton Courthouse in wintertim
Warrenton Courthouse in winter.

Established in the 1700s as a little trading post called the Red Store and incorporated in 1810, the town was named after General Joseph Warren, a Revolutionary War hero. Having gone through decades of wars, fires, scandal, and rebuilding, Warrenton emerged as one of Virginia's most beautiful places in America with a tasteful mix of old, new, historical, and urban. From the town's earliest years, the impeccable-preserved courthouse and old jailhouse are museums of Civil War exhibits, jail cells, and Native American artifacts. The 19th-century buildings on the streets have maintained their original facades, now housing galleries, boutiques, and specialty shops. There are also haunted houses, engaging museums, and the Whitney State Forest nearby for camping and hiking in the fresh air.

Clearly, Virginia has a lot to offer in terms of outdoor pursuits with its myriad of hiking trails and mountain vistas to entice the most weathered travelers. With quintessential characters and the quaintness of the small town living, the atmospheric downtown areas brim with the history and culture of the region, along with the southern charm in the local eateries and boutiques.  

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