Updated Sep 7, 2023

Take This Road Trip Through Virginia’s Most Picturesque Small Towns For An Unforgettable Experience

A curated road trip through Virginia's small towns offers breathtaking sites and local charm.

Updated Sep 7, 2023

Written by

Beth Copenhaver

Trip Ideas|Road Trips

Published Oct 17, 2024

The Scenic Road Trip That Leads to 5 of Virginia’s Most Charming Small Towns

Check out five of Virginia's coolest small towns in this epic multi-day road trip.

Published Oct 17, 2024

Written by

Lisa Sammons

Don't you just love a small town? Virginia's larger cities are incredible - I love a day trip to Richmond, and Norfolk and Chesapeake both have their charms. But small towns make up the backbone of our great state, and any visit to Old Dominion is incomplete without checking out some of our many little rural towns. They're perfect for discovering the state's rich culture and history, and also a wonderful place to find great little shops and restaurants. If you're looking for your next big adventure, we've got a great one in store for you today with this epic road trip to some of the best small towns in Virginia. This is a lengthy trip, but it's full of fun and perfect for next time you've got a few days free.

If you opt to explore the entirety of the trip we have planned, it'll take just under five and a half hours of driving. Of course, you'll want to add in a few hours to explore each town. I recommend allotting at least three days for the entire trip, but you can always customize the itinerary using Google Maps if you're looking to make the route shorter.

We'll start our trip in Front Royal, a town of 15,000 in the Shenandoah Valley. It may have a somewhat sizable population to be included on a small-town road trip list, but you'll find that this place has all the charm of a much tinier city. This is an absolutely beautiful spot, and one of our favorite restaurants to enjoy here is Region's 117, an exquisite eatery offering up lakefront fine dining with incredible views. Love history and all things spooky? Check out Prospect Hill Cemetery, an allegedly haunted graveyard that's the final resting place of many Civil War soldiers.

alt — Street scene in downtown Culpeper, Virginia, a Second Amendment sancuary some 75 miles (120 kilometers) from Washington, DC on January 16, 2020. – When Sheriff Scott Jenkins swore to protect the US Constitution, he swore to uphold the second amendment — and that means guaranteeing citizens the right to bear arms, even as the Virginia government weighs depriving state residents of what Jenkins considers an inalienable right.
“The Constitution is very clear: the second amendment grants every citizen to bear arms, specifically against a tyrannical government,” said the officer from Culpeper County, a rural region about 60 miles (100 kilometers) southwest of Washington.
Since December, he has become a key figure in a pro-second amendment protest movement that has organized a protest in Richmond, the state capital, on January 20, 2020. At least 10,000 supporters plan on attending, according to media reports.
The second amendment, which says that “the right of the people to keep and bear Arms, shall not be infringed,” has proved controversial over the years and has been subject to many different interpretations. The Supreme Court has ruled that individuals have the right to keep firearms in their households, but left it to states to determine how the weapons could be transported. (Photo by EVA HAMBACH / AFP) (Photo by EVA HAMBACH/AFP via Getty Images)

Head south a bit, and you'll hit our next destination, Culpeper. This is another bigger-than-it-feels town, and you'll be welcomed by a bustling downtown area that offers a little bit of everything. You'll find charming little cafes and shops lining the city streets. The quiet setting in the Blue Ridge Mountains provides plenty of natural beauty, and the city's outskirts boast gently rolling hills and tranquil farmlands.

Those who prefer their small towns a bit smaller will love our next stop: Ashland, population 7,000. This historic town has plenty of ties to the railroad, and its visitors center is housed in an old 1920s train station. Looking for a unique dining experience? Check out Islamorada Fish Company. The rustic atmosphere and giant aquarium make for quite a memorable meal.

alt — FARMVILLE, VA – NOVEMBER 17
The rural town of Farmville, VA, is home to Fuqua School on November 17, 2011, in Farmville, VA. Fuqua School is one of the former segregation academies in Virginia which are now actively recruiting black students. The school was founded in 1959 as Prince Edwards Academy, a segregation academy set up for white students to be educated when Prince Edwards County Schools closed rather than integrate after the Supreme Court’s decision in Brown vs Board of Education. In 1986, the school ended its discrimination policies and began accepting non-white students.

You'll head southwest a bit before coming up on our next town: Farmville (no, not the Facebook game!). As the name implies, this is a farm town through and through, and it's the perfect place for a quiet escape. It's a two-college town that's home to Longwood University and Hampden-Sidney, but it's perhaps best known for its furniture shopping. The sprawling Green Front Furniture has over 1,000,000 square feet of luxury furniture available in 12 warehouses spread out over six blocks. Another can't-miss attraction here is High Bridge Trail State Park, home to a 31-mile trail running over the Appomattox River.

alt — Bruce Yuanyue Bi/The Image Bank/Getty Images

Last but not least is our final stop on this road trip: Lexington. This city lies right at the intersection of Interstate 81 and Interstate 64, and has so many great attractions. This is another two-college town: it's home to both the Virginia Military Academy and Washington and Lee University. The downtown area contains several historic Civil War sites, including Stonewall Jackson's house and gravesite.

Which of these small towns in Virginia is your favorite? Any that aren't on the list that you think should've been included? Share your thoughts in the comments!

Traveling by car is my favorite way to explore: it offers up so many opportunities to check out unexpected wonders! With that being said, road trips do require a bit of extra preparation. To make sure you stay safe and have a great time, check out our road trip essentials packing list before hitting the highway.

Trip Ideas|Small Towns

Published Sep 19, 2024

The Fastest-Growing City in Virginia That’s Perfectly Sized

It's not far from the Nation's Capital, but the reason Winchester, Virginia is one of the fastest-growing regions of the state goes beyond the hustle and bustle of the city.

Published Sep 19, 2024

Written by

Beth Copenhaver

Northern Virginia is often thought of in terms of its proximity to Washington D.C. And yet the fastest-growing region of the state, while it isn't far from the nation's capital, is appealing for more reasons than its convenience to DC. Winchester and Frederick County have made significant population gains over the past few years, more so than any other region of Virginia, in fact. Since 2020, this area has seen a population growth of 5.4%. And sure, it doesn't hurt to be close to a metropolis, but what locals love about Winchester and the surrounding area is its small-town feel complete with delightful local attractions and access to the great outdoors.

alt — thomas porter / 500px / Getty Images

Ask locals what they love most about living in a place like Winchester and you'll get a host of different reasons. But it seems to boil down to a common theme: balance. It's sizable, but not too big. It's close to Washington, D.C., but has everything you need in town so braving the traffic into the city isn't always necessary. There are enough locals that the town feels busy, but never over-crowded.

For outdoor enthusiasts, the location is ideal. Just a 30-45 minute drive will land you in the Blue Ridge Mountains or the Appalachian Trail. It's even close to West Virginia's Tuscarora Mountains.

And then there's the history. It's the oldest incorporated city in Virginia west of the mountains, with its founding dating back to 1744. Prior to that, it served as significant land and a camping ground for the Shawnee. George Washington spent time in Winchester and even set up an office there. It's also the birthplace of country music star, Patsy Cline.

The history becomes apparent as you make your way through Old Town. Some must-see landmarks include the Handley Regional Library, Old Court House Civil War Museum, Museum of the Shenandoah Valley, and George Washington's Office Museum.

Of course, there's plenty to do in Winchester, too. Aside from the famous Shenandoah Apple Blossom Festival, there are countless live music and community events to enjoy. Traveling with kids? We'd recommend a trip to the Shenandoah Valley Discovery Museum, an ice cream cone from Red Fox Creamery, and a trip to a local apple orchard.

Have you visited Winchester, Virginia lately? What were some of your favorite attractions and activities? Feel free to share them with us -- we would love to hear from you! And, if you need the perfect home base for your adventures, check out these unique places to stay in Winchester, Virginia.

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Take This Road Trip Through Virginia’s Most Picturesque Small Towns For An Unforgettable Experience

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The Scenic Road Trip That Leads to 5 of Virginia’s Most Charming Small Towns

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The Fastest-Growing City in Virginia That’s Perfectly Sized

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All Stories

The Panoramic-View Restaurant on Lake Erie in Pennsylvania Is a Must-Visit

If You Only Have One Day to Visit This Small Town in Connecticut, Here’s Everything You Absolutely Can’t Miss

Hike the Port Penn Wetlands Trail in Delaware for an Unforgettable Adventure

The Remote Work Retreat Center in New Hampshire You Will Never Want to Leave

We Explored a Cave and a Waterfall Along this Easy Tennessee Hike