6 Bucket-List Small Towns In Virginia
Virginia is home to so many bucket-list-worthy small towns that you could easily fill a book with them. Boasting fascinating colonial pasts stretching all the way back to the country’s first English settlers in 1607, the Commonwealth’s must-visit towns have featured prominently in everything from the Revolutionary War to cultural revolutions in music and the arts. Whether you’re interested in visiting preserved battlefields, following the state’s country music trails, or seeking some outdoor adventure, these six towns provide truly authentic Virginia experiences that are worth adding to your bucket list.
Danville
Known as the City of Churches for its more than 100 houses of worship, the former tobacco town of Danville is a lot of fun to explore on foot. Downtown Danville centers around the River District, a pedestrian-friendly area where 19th- and early 20th-century tobacco warehouses still dominate the townscape.
Stretching from Main Street east along Bridge Street, the River District is where you’ll find the Crossing at the Dan, an impressive old tobacco industry structure that’s now used for public events like the Danville Farmers' Market. The adjacent Danville Science Center is also a part of the Crossing and features cool interactive displays about topics such as water, energy, and even the cosmos (be sure to visit The Dome with its state-of-the-art digital experiences).
From here, you can also enjoy the Riverwalk Trail, an 11-mile-long paved walking and biking path that follows the Dan River. The trail passes over an old railroad bridge from the River District, with a shorter loop walk crossing back over one of two bridges carrying Main Street back to the River District. The nearby Bee Hotel occupies the town’s old newspaper offices and offers boutique-style accommodations within sight of the river.
If you’ve energy left, follow Main Street up to Millionaire's Row. Here, impressive Victorian and Edwardian mansions once owned by the town’s wealthy make for an extremely pretty backdrop at any time of year. Dominating Millionaire's Row, the views from Mount Vernon United Methodist Church back along Main Street cement Danville’s reputation as a bucket-list worthy destination.
Onancock
When exploring the Chesapeake Bay and the deep waters of Onancock Creek in 1608, Captain John Smith was so impressed by the area’s potential for settling that he declared it "the Gem of the Eastern Shore." He was right. Onancock’s strategic location and its deep, protected harbor just four miles inland from the Bay saw it become an important commercial and fishing hub, only surpassed by Cape Charles to the south after the arrival of the railway in the 1800s.
Wander through Onancock Historic District these days, and you’ll see many fine examples of Federal and Victorian-style stores and homes built in the town’s heyday. Standouts include the Roseland Theatre from 1913, and Hopkins & Bros. Store, constructed in 1842 overlooking Onancock Harbor.
You can even get a taste of what Smith would have seen by renting a kayak from Burnham Guides Paddle & Bike or hopping aboard a ferry for a trip across Chesapeake Bay to the remote fishing community of Tangier Island.
Ker Place, built in 1799 and now a museum, is not only nice to look at, but features interesting exhibits on steamboat travel, oystering equipment, and the area’s native Accomack tribe. Just a short stroll away, the elegant Victorian-era Onancock Inn offers bed and breakfast style accommodations, while the Onancock Taphouse is a great place to connect with locals and great beer.
Floyd
You’ll no doubt have heard of Floyd if you’re a die-hard old-time music fan. A must-stop along the Crooked Road (aka, the 330-plus mile long Virginia Heritage Music Trail), this small town has become famous for its role in preserving the Appalachian musical traditions of bluegrass and mountain gospel.
Plan to visit on a weekend, and you can enjoy the fun Friday Night Jamboree held in Floyd Country Store. Built in 1910 and bursting at the seams with music fans when Friday rolls around, everyone gets up and dances here, regardless of age or ability.
And when they’re not dancing, visitors wander along Locust Street, tapping and clapping along to impromptu sing-alongs as young and old alike strum away. It's truly a magical and heartwarming experience.
If you do plan on staying a night or two, book a room at Hotel Floyd. It’s not only near all the music fun, but also just a short walk away from Floyd Farmers Market and the Floyd County Historical Museum.
Bristol
Named after the port city in England, Bristol holds the unique distinction of spanning two states. Its main street, the aptly named State Street, serves as the state border and literally divides the town in two, with Virginia on one side of the road and Tennessee on the other. If you get confused after visiting watering holes like O'Mainnin's Pub or Stateline Bar & Grille, handy brass markers in the pavement will remind you which state you’re in.
And if you’re wondering why Bristol has so many bars, it has a lot to do with its being known as the “Birthplace of Country Music.” In fact, country music’s roots go back 99 years to 1927 when the now legendary recording sessions introduced Jimmie Rodgers and the Carter Family and their music to the world.
Recorded by the Victor Talking Machine Company in a building that once stood on State Street (it’s now a car park, but a plaque lets you know you’re in the right place), these landmark recordings had a huge impact on American music. The country, bluegrass, and folk music you hear today can all trace their existence back to Bristol’s famous “sessions.”
Related must-visits include the Birthplace of Country Music Museum, a Smithsonian affiliate that uses immersive exhibits and listening stations to present country music's evolution from its Appalachian folk roots right through to today’s stars. Sessions Hotel, named in honor of the 1927 recordings, is the perfect place to stay while you explore bucket-list Bristol. Spread across a former candy factory and mill built in the 1920s, it’s also made a name for itself as a concert venue.
Charlottesville
No college campus in the United States can quite match that of the University of Virginia in Charlottesville. Founded by Thomas Jefferson in 1819 and now a UNESCO World Heritage Site (that alone tells you it’s special), the Academical Village is considered a masterpiece of American design. And it’s a delight to explore on foot.
Highlights include the spectacular Rotunda. Set at the far end of the magnificent Lawn, this impressive building was designed with a nod to Rome's Pantheon and completed in 1826. The Lawn, a wide, grassy corridor flanked by the original pavilions, which senior students still compete for, deserves to be explored.
The Downtown Mall, a seven-block pedestrian zone along Main Street, is a car-free zone that also deserves a look. Here you’ll find landmarks like the New Dominion Bookshop, around since 1924, and the historic Paramount Theater, a restored 1931 movie palace that hosts films and concerts.
Jefferson's nearby mountaintop plantation, Monticello, is a must-visit. Tours of his former home include the chance to explore the grounds and other buildings, including slave quarters.
Wytheville
If you’ve ever whizzed past Wytheville and never stopped, you’re in for a very pleasant surprise. Downtown Wytheville has long been a crossroads for travelers and is once again making a name for itself as a bucket-list small town. It even boasts a connection to the White House. Edith Bolling, later famous as First Lady Edith Bolling Wilson, second wife of President Woodrow Wilson, was born here in 1872, and is celebrated at the Edith Bolling Wilson Birthplace Museum.
Directly opposite, The Bolling Wilson Hotel (yes, it’s named for the former First Lady) is a great base from which to explore Wytheville. The hotel's Graze on Main is a good choice for dining, as is the quirky Log House 1776 Restaurant, a little further along Main Street. Part casual dining, part antique and collectible store, the food’s delicious.
Speaking of unique dining, check out Wohlfahrt Haus Dinner Theatre. Located between the downtown and the Interstate highways, this first-rate professional theatre company features Broadway-style musicals along with tasty grub.
Virginia's Bucket-List Small Towns
From Danville’s revitalized tobacco warehouses to Onancock’s beautiful Chesapeake Bay setting, and from the Appalachian heritage of Floyd to the country music rhythms of Bristol, these six Virginia small towns are without a doubt bucket-list caliber. Add them to your list of must-visit destinations in “The Old Dominion” and prepare to be impressed.
