11 Stunning Small Towns In Virginia
Virginia is home to a wide array of stunning small towns. In the southwest, you can roll into trail towns like Damascus, where thru-hikers crowd the sidewalks, and a famous downhill bike ride drops you straight into the middle of Main Street. Farther east, in Chincoteague, the vibe changes to salt air and seafood. And in between, you’ve got the historic buildings in Smithfield and captivating mountain energy in Front Royal that puts Skyline Drive and Shenandoah right on your doorstep. These towns, and a few others, make the trip to Virginia worth your while.
Williamsburg
Located on the Virginia Peninsula, this small town is best known as the home of Colonial Williamsburg, the largest living history museum in the world, and one of the vertices of Virginia’s Colonial Triangle. The carefully restored 18th-century buildings and costumed interpreters provide a window into US history and transport visitors back to the days of the American Revolution.
Beyond the abundant historical attractions, Williamsburg is also home to Busch Gardens Williamsburg, a 130-acre, European-themed amusement park that features world-class roller coasters, live entertainment, animal encounters, and delicious food. The park has been voted “World’s Most Beautiful Amusement Park” every year since 1990. Williamsburg also fashions itself as the Pancake Capital of the World, with around a dozen different pancake houses within the city limits. Williamsburg also hosts its own pancake festival in September, which offers discounts, live entertainment, and hours of fun for the whole family.
Staunton
Staunton is located along the I-81 corridor in western Virginia. It is most notable as the birthplace of former president Woodrow Wilson, and visitors can tour his childhood home, known as The Manse, and learn more about his presidency and life at the Woodrow Wilson Presidential Library and Museum. The town is also home to the American Shakespeare Center, a theater troupe that performs at the Blackfriars Playhouse, a replica of William Shakespeare’s Blackfriars Theater. The group produces around eight shows each year, focusing on the words of the Bard and his contemporaries.
Staunton’s downtown is gorgeous, with over 200 of its buildings designed by Thomas Jasper Collins in the 19th Century. Several of his buildings, including the Augusta County Courthouse, are listed on the National Register of Historic Places. Ski bums will also love Staunton for its proximity to the Wintergreen Ski Resort, a four-season ski destination on the eastern slopes of the Blue Ridge Mountains, less than 45 minutes from downtown.
Damascus
Virginia is home to 544 miles of the Appalachian Trail, more than any other state, and Damascus is the first town northbound hikers will pass through after crossing the border from North Carolina. It is, therefore, no surprise that much of the town’s identity is closely linked to hiking and the outdoors.
In addition to the Appalachian Trail, Damascus also sits along the Virginia Creeper Trail, a 34-mile rail-to-recreation trail that runs from Whitetop to Abingdon. The trail is best known for the incredibly popular, and easy on the quads, 17-mile downhill stretch from Whitetop into the heart of downtown Damascus. Its proximity to the Mount Rogers National Recreation Area makes it an ideal starting point for peak baggers looking to summit Mount Rogers, the highest mountain in the state.
One of the town’s most popular events is the annual Trail Days Festival each May, which draws an estimated 25,000 people to the tiny town for a celebration of Appalachian Trail and hiking culture. The event features live music, hundreds of vendors selling handmade goods and outdoor gear, and one of the largest gatherings of thru-hikers, past and present, anywhere in the world.
Smithfield
If you like ham, you will love this tiny town in Isle of Wight County. Known affectionately as “Hamtown,” Smithfield’s main claim to fame is its eponymous Smithfield ham, known for the distinct flavor imparted by the hogs’ diet of peanuts. Smithfield has several pork-centric attractions, including statues of market hogs painted by local artists spread across the town, and the world’s oldest ham, a century-old beauty on display at the Isle of Wight Museum. Smithfield takes its ham so seriously that it is illegal to advertise a ham as a Smithfield ham unless it is produced within the town limits.
Vegetarians and the generally ham-averse need not fear, however. Smithfield’s rich history provides a more than adequate non-porcine itinerary. The town boasts an array of architectural styles, from Victorian-style gingerbread to Gothic cottages, and the historic district contains several buildings on the National Register of Historic Places, including the P.D. Gwaltney Jr. House and the Old Courthouse of 1750.
For nature lovers, Windsor Castle Park provides numerous opportunities for outdoor recreation. With 208 acres of green space along the Pagan River, visitors can hike along the woodland trail system, kayak in Cypress Creek, or try to spot wildlife from the Eagle Nest observation platform.
Chincoteague
Chincoteague encompasses the whole of Chincoteague Island on Virginia’s Eastern Shore and is one of the most unique and serene beach resorts in the country. The town itself contains several historic inns, bed and breakfasts, and is the birthplace of Island Creamery, a chain of ice cream stores on the Delmarva Peninsula. The original Island Creamery has been open since 1975 and is a staple of the region.
The island is best known as the gateway to the Chincoteague National Wildlife Refuge on Assateague Island, over 14,000 acres of federally protected marshland, forests, and beaches operated by the US Fish and Wildlife Service. The refuge draws millions of visitors every year, making it one of the most visited wildlife refuges in the country, and is home to the historic Assateague Lighthouse, miles of hiking trails, and a herd of feral Chincoteague ponies made famous by Marguerite Henry’s book Misty of Chincoteague. Local legend has it that the horses are descended from survivors of a shipwreck off the Virginia coast, but there are no historical records to confirm this harrowing tale. Every year in July, the ponies take part in a Chincoteague tradition known as the Pony Swim, where the horses are herded from Assateague Island to Chincoteague Island. The festival celebrated its 100th anniversary in 2025.
Tangier
Visitors to this island may feel like they stepped back into the 18th century when they hear the dialect still spoken in this small town. Described as a blend of Tidewater twang and colonial brogue, the accent is as unique as the island on which it is found.
Located on an island in the middle of the Chesapeake Bay, there are no roads to Tangier. If you want to visit, you will need to take a boat or a small airplane from the mainland. Once on the island, you will find that there are a few cars, and most locals use bikes or golf carts to get around. The Tangier History Museum is an excellent resource for learning about the island’s history from John Smith, the first European visitor, to its British occupation during the War of 1812. Tangier also offers some of the most breathtaking views of the Chesapeake Bay and numerous opportunities for wildlife viewing along the island’s shore.
Big Stone Gap
Located just outside of the Glades Wildlife Management Area in southwestern Virginia, it should come as no surprise that the main attraction here is the miles of unspoiled nature just a short drive away. Some highlights include Natural Tunnel State Park, an 850-foot-long, 10-story-high tunnel carved by nature through limestone, and the High Knob Observation Tower, which offers panoramic views of the surrounding mountains.
The town is also a convenient starting point for hikers hoping to see The Devil’s Bathtub, one of the most popular and picturesque swimming holes Virginia has to offer. The aquamarine pool, cascading waterfalls, and dense deciduous forest provide an excellent destination for a day trip from town.
For those wanting to stay closer to civilization, the Southwest Virginia Museum is an excellent place to learn about the region's history from pioneer times to the 19th-century coal mining boom. Big Stone Gap also hosts several annual music festivals, including the Mountain Music Heritage Week every October.
Cape Charles
Overlooking the mouth of the Chesapeake Bay on the Southern end of Virginia’s Eastern Shore, Cape Charles owns one of the only two public beaches on the peninsula and the only one on the scenic bayside.
Surrounded on three sides by water, the town is a beach-lover’s paradise. The Cape Charles Fishing Pier extends 300 feet into the bay and provides a free fishing spot for locals and tourists alike. The nearby Cape Charles Natural Area preserve is a wonderful spot to hike along the elevated boardwalks through the scenic forested uplands. The area serves as a sanctuary for the extremely rare northeastern beach tiger beetle. Birdwatchers flock to the area in the fall, when the trees become a temporary habitat for songbirds and raptors on their way south for the winter.
Just a short drive away, Eyre Hall, one of Virginia’s most picturesque colonial homes, sits on the shores of Cherrystone Creek. The house, constructed in 1760, is only open to the public during Virginia’s Historic Garden Week, but the parterre gardens, some of the oldest in the country, may be visited year-round.
Front Royal
Just 70 miles west of Washington, DC, Front Royal is the northern terminus of Skyline Drive and serves as an excellent gateway for visitors hoping to explore Shenandoah National Park along one of the most scenic roads in the country. Constructed by the Civilian Conservation Corps in the early 20th century, this scenic byway traverses 105 miles along the crest of the Blue Ridge Mountains and is the only public road through the park. It takes about three hours to drive the entire road one-way, not counting the time spent stopping and gawking at the serene majesty of the mountain vistas.
For those with more subterranean proclivities, Skyline Caverns is the perfect attraction to scratch your speleological itch. First discovered in 1937, the caverns are one of the few places in the world where you can see anthodites, unique crystal formations whose needle-like spikes radiate in all directions. One of Skyline Caverns' main attractions, a formation called The Chandelier, is believed to be the largest anthodite ever discovered.
After a hard day of exploring the outdoors and underground, drink in the craft beer scene at one of the numerous breweries that line Historic Main Street. Front Royal is also home to the Virginia Beer Museum, where visitors can learn about the 400-year history of beer.
Wytheville
Wytheville is tucked away towards the end of I-81 in the Southwestern tip of Virginia, about 30 miles from the North Carolina border, and is known as the Crossroads of Southwestern Virginia. Named for George Wythe, one of the signers of the Declaration of Independence, the town has a rich history that can be explored in depth at the Thomas J Boyd Museum. The museum houses an extensive collection of artifacts from the American Civil War and exhibits about the Wythe County Polio Epidemic in 1950. The town is also the birthplace of former First Lady Edith Bolling Wilson, and her childhood home now contains a museum dedicated to her life and legacy.
For great views of the rolling foothills that surround the town, the Big Walker Lookout, a 100-foot-tall observation tower, is one of the tallest in the state and affords a stunning 360-degree view of the Blue Ridge Mountains. If you are feeling a mite vertiginous after climbing to the top, check out Wytheville’s Smallest Church, a tiny little prayer chapel located just off I-77.
Bristol
Another Southwestern Virginia gem lies just across the border from its twin city: Bristol, TN. The Tennessee-Virginia border runs right down Bristol’s State Street, affording a unique opportunity to walk across the street into a completely different state.
The town is officially recognized as “The Birthplace of Country Music,” per a resolution passed by the US Congress in 1998, and fans of country music history should be sure to check out the aptly named Birthplace of Country Music Museum to learn about the role the region played in creating one of the most enduring genres of American music.
The Bristol Railroad Station, listed on the National Register of Historic Places, hasn’t been an active railway stop since 1971, but the distinctive and beautiful building now serves as a meeting location for local organizations and an event space. Extraterrestrial enthusiasts may want to visit Bristol in June for the annual Saucers Over Appalachia Festival dedicated to the region's UFO history.
Stunning Virginia Scenery
Featuring stunning mountain ranges, fertile valleys, and incredible ecological and geographic diversity, Virginia has an attraction for every type of traveler. Whether you like hiking in the verdant hills of Shenandoah or relaxing on the shores of the Chesapeake Bay, exploring America’s Revolutionary War history, or learning about one of the eight US presidents born in Virginia, these small towns will provide unforgettable travel experiences for those willing to take the smaller roads for a while.
