15 Best Small Towns to Visit in Virginia

One of the original states settled by the first Europeans to cross the Atlantic, Virginia has both a spectacular coastline and majestic mountains that hold some of the history of the beginning of the United States. This state has something for everyone: boutique wineries and breweries, a host of outdoor sporting activities, and charming towns filled with shopping and local restaurants that will not disappoint. Brush up on your history and take a step away from modern life when you visit Virginia’s rural towns. Be sure to enjoy the local color and pack light – leave your worries at home and relax.

Check out our list of the best small towns to visit in Virginia:

1. Abingdon, Virginia

Located in Washington County, Virginia, Abingdon is home to a thriving artist community and a designated Virginia Historic Landmark. Here, they built Black’s Fort to protect settlers during the Revolutionary War, and from attacks from neighboring tribes. Now, it’s a prime vacation destination in the Appalachian mountains.

For hiking enthusiasts, Abingdon is the end of the Virginia Creeper Trail, a 35 mile long hike that winds along Whitetop Mountain. Walk along the historic Main Street and visit landmarks such as Martha Washington Inn. You can even book yourself a few nights here and continue browsing the local artists galleries or the William King Art Museum. Don’t forget to catch a show at the Barter Theatre, or attend the Virginia Highlands Festival, a local showcasing of Appalachian art. Take a trip down Crooked Road and through time and learn about the mountain peoples music and traditions before departing from Abingdon.

2. Bristol, Virginia

Literally a town split between Tennessee and Virginia, the state line runs down Main Street. Located along the famous “Crooked Road”, Bristol is known as the birthplace of country music. For all those country music fans, it is a must-see; the first country music recordings for national distribution were recorded here. Stop in at the Birthplace of Country Music Museum or hear some live music.

If you aren’t as interested in country music, you can go horseback riding or hiking here. Head out to the Bristol or Appalachian Caverns as well – the nature is just as beautiful as the country music! Right across on the Tennessee side, you’ll find the Bristol International Speedway for all those Nascar lovers.

3. Culpeper, Virginia

A fun fact: Culpeper, located in Culpeper County in Virginia, was originally surveyed by a young George Washington! Later, the town sheltered pro-Independents during the Revolutionary War. A perfect weekend getaway for the history buff, there are plenty of quaint Bed and Breakfasts to stay at in town.

Visit the Old House Vineyards or the Belmont Farms Distillery and sample some of the local offerings. Moonshine is even made legally at Belmont, and is the only distillery in the state permitted to do so! Or, walk around Main Street, revitalized after the Virginia Main Street program, and do some shopping at the local stores, then visit the Museum of Culpeper History. After you’ve seen the historic homes and churches, see a horse show at Commonwealth Park.

4. Farmville, Virginia

Farmville, Virginia - High Bridge Trail State Park — Farmville, Virginia – High Bridge Trail State Park

Not to be confused with the once popular Facebook game, Farmville is a town located along the Appomattox river and High Bridge Trail State Park. A growing community that still retains a laid back rhythm, Farmville is a great place to escape if you have a few days off.

Take a day and walk the High Bridge Trail State Park, which is approximately 4 miles long and ends at the historic High Bridge, or stay in town and check out the Farmville Historic District or the Sayler’s Creek Battlefield. Farmville also hosts the Heart of Virginia Festival every year, a festival that celebrates local traditions and offers a fireworks show. If you can’t make that, stop in on a first Friday of the month to catch the concerts and town festivities at Riverside Park.

5. Damascus, Virginia

Virginia Creeper Trail, Damascus, Virginia

Located in the mountains in Washington County, Damascus is at the convergence of 4 popular hiking trails: The Appalachian Trail, the US Bicycle Route 76, The Iron Mountain Trail and The Virginia Creeper Trail. Be sure to bring your hiking boots when you come out here, and don’t forget the camera!

Damascus hosts the Trail Day Festival in May, the largest festival for Appalachian hikers in the country. Even if you are not an avid hiker, the rustic beauty surrounding Damascus is enticing. Stay at a local cabin and kick back after hiking or biking, or even kayaking on the river. Stop in for a coffee at Mojoe’s Trailside Cafe and Coffee house and chat with the locals or any of the intrepid hikers passing through. Truly laid back, you can walk through town and get to know the locals sitting out on their porches or enjoy a relaxed meal at the local restaurants.

6. Gordonsville, Virginia

Located in Orange County (the Virginia Orange County, not the one in California), Gordonsville is slightly northeast of Charlottesville. The town hit its two hundred year anniversary mark in 2013, commemorating the date that Nathan Gordon, a local innkeeper, was appointed postmaster to the area. It also had historical significance during the Civil War due to its proximity to the Virginia Central Railroad.

Refresh your history knowledge as you walk through Gordonsville. Nathan Gordon’s original tavern, which burned down and was rebuilt as a hotel before the Civil War, became an army hospital and treated more than 70,000 patients. It’s now the Civil War Exchange Museum and is worth a visit. The Confederate army was able to mostly defend this town during the Civil War, leaving it largely unscathed. Stop in at the local shops and galleries for some lighthearted fun or explore the scenic countryside and mountains by foot, bike or horseback if you don’t want to take a car out.

7. Lexington, Virginia

Named after Lexington, Massachusetts, where the first shots of the Revolutionary War were fired, Lexington, Virginia has also played a significant role in American history: Confederate generals Robert E. Lee and Stonewall Jackson are buried here, and Stonewall Jackson’s house is now open to the public as a museum. Cyrus McCormick even invented his machine powered reaper here, and his farm now belongs to Virginia Tech.

Visit Lexington and revisit some historic Civil War sites, and military museums. The downtown area itself is a historic district with charming shops and restaurants frequented by locals and visitors alike. It has even been involved in filming some Hollywood movies: Brother Rat, with Ronald Reagan, and Sommersby, with Richard Gere, to name a couple. Whether a history or movie buff, this town has a lot to offer any visitor.

8. Manassas, Virginia

For those who remember their US History courses, the Battle of Manassas was fought here nearby and was the first major battle of the Civil War. Also known as the Battle of the Bulls, there was a second battle fought there two years later. A strategic location because of the railroad crossings, Manassas was mostly held by the Union army except for those key battles.

Nowadays, people come to Manassas to retrace steps in history and see these battlegrounds, but there is also more to offer in this town. After you’ve seen the battlefield, check out the Manassas Museum or Train Station, and mull over your newfound historical expertise when drinking a cool beer at Heritage Brewing Company. The historic downtown area offers many shopping options as well.

9. Occoquan, Virginia

Occoquan is located in Prince William County, Virginia, right next to Washington D.C. If you’re seeking a little peace and quiet after the hustle and bustle of the capital, you’ve come to the right place. Derived from an Algonquian word meaning “end of the water”, it lies along the Occoquan River and was a central trading point for the Native Americans and later the Europeans.

Today, Occoquan is a charming artist’s community, with a historic downtown area and plenty of shops and dining to keep you busy. Spend some time walking along the river and down to the port, or if you’re feeling brave, take one of their famous ghost walks. You can always relax later at the Dansk Day Spa if you find the experience too frightening.

10. Onancock, Virginia

Originally a port town, Onancock is located along the banks of Virginia’s Eastern Shore. With great waterfront views, downtown Onancock is lined with trees and beautiful Victorian houses. It’s a lively area with live music on the weekends and a variety of shops that are sure to delight any visitor, with high end accommodations begging you to treat yourself to some R&R.

Book a few days at Charlotte Hotel, a high end hotel and explore the artists’ exhibits, and walk along the Eastern shore. It’s close to Chincoteague and the wild ponies as well! Have a coffee at Bizzotto’s Gallery Cafe before walking down to the wharf for some fresh air. Take a boat out on the water and enjoy the sunset before heading back into town.

11. Orange, Virginia

Orange is the county seat of Orange County, Virginia and was founded in the 18th century. Strategically important during the Civil War, it also served and Robert E. Lee’s headquarters from 1862-1864. You can still visit the St. Thomas Episcopal Church where he worshipped during that time if you’re interested.

Visit the historic downtown area and check out the county Courthouse before staying a few nights at the Holladay Bed and Breakfast. Once you’ve explored the downtown area, visit the James Madison Museum or go see his old plantation home a few miles away, Montpelier. Take a kayak out on the Rapidan River or stop in and have a glass at the local wineries.

12. Chincoteague, Virginia

The island made famous in Marguerite Henry’s book, Misty of Chincoteague, the town Chincoteague actually has no ponies, as those are located on the nearby island of Assateague. Legend has it that those ponies survived a Spanish galleon shipwreck. Don’t miss out on their Pony Penning Day, when they round up the feral ponies who then swim the shallow channel between the two islands.

Spend some time here at the beach soaking up the ocean air, and explore the town’s specialty shops and ice cream parlors. Chincoteague takes you back to a simpler life, and invites you to relive that magic that children felt when reading Misty of Chincoteague. Stay at a local bed and breakfast or bring your camping gear if you’re feeling adventurous.

13. Washington, Virginia

Shenandoah National Park, Washington, Virginia

Named after George Washington and located in Rappahannock County, Washington was also surveyed by THE George Washington in 1749, but is not to be confused with Washington D.C, which is 70 miles away. During the Civil War, this town also had a hospital for wounded soldiers on Main Street.

Following that time in history, very little has changed in Washington. It really feels like you’re going back in time to a rural town. Leave your technology in the city and head out here for a weekend of disconnecting. You can even do so in style: The Inn at Little Washington is a luxury hotel and five star restaurant. Enjoy some delicious meals and explore the little artist shops this town invites you to discover.

14. Woodstock, Virginia

A town in the Shenandoah County, Woodstock did not host that infamous love festival of the sixties but has placed a significant role in history nonetheless. As legend has it, at the start of the Revolutionary War, a local pastor finished his sermon one Sunday, then removed his clerical robes to reveal a uniform underneath, calling the men to fight for their new country.

Nowadays, you can visit the historic downtown and see the oldest courthouse still in use west of the Blue Ridge Mountains, a limestone building initially commissioned by Thomas Jefferson himself! Stop over in this town to learn about its history and, if you have time, go to the Woodstock Shenandoah Museum or have a drink at the Woodstock Brewhouse.

15. Wytheville, Virginia

In the southern Blue Ridge Mountains, Wytheville is named after one of the signers of the Declaration of Independence, George Wythe. This town boasts a fascinating Historic District and a lively small town charm that is sure to entice you to stay awhile.

Stop by the local markets to try the locally source foods, or bring your motorcycle and explore the many motorcycle trails around the town. If you’d prefer to leave the wheels at home, walk around town to catch a dinner theatre show at the Wohlfahrt Haus Dinner Theatre or listen to some live music at a local watering hole. There are also great fly fishing opportunities for the fishermen and many nature hikes for those so inclined. A unique name for a unique town, Wytheville knows how to show you a good time.