10 Best Small Towns in Virginia
Whether you’re looking for a short getaway or a forever home, these small towns in Virginia hold many surprises.
Even though I’ve lived in Virginia my entire life, I still have yet to scratch the surface of the charming towns within this beautiful state.
Since everything is opening up now, no time like the present to book a memorable trip with your family and friends.
From the coast to the mountains, Virginia is sure to have a town that suits your preferences whether you’re thinking about moving here or visiting for a few days.
Come across beautiful animals and beautiful landscapes with history waiting to be explored.
There’s no denying that Virginia is a historical place with events that have shaped the United States like battles and museums.
Here are the small towns in Virginia that I recommend!
1. Culpeper
Culpeper is a laid-back town that is increasingly becoming popular with tourists. Due to its close proximity to Washington D.C, it is one of the best towns to stop and explore for a few hours before hitting the bustling city.
One of the best things to do in Culpeper is to check out their wineries including the Mountain Run Winery and Old House Vineyards.
You can even stop by Flavor on Main and Piedmont Steakhouse for a delicious meal. Besides the restaurants and attractions, the town is known for being super friendly and the perfect place to raise a family or explore.
While Culpeper may have its fair share of beautiful parks, it is also a small town that offers so much more.
Visitors can take a tour of the Burgandine House or stop by The Frenchman’s Corner of Culpeper for French pastries and chocolate.
Did you know that Culpeper was the last county in Virginia to integrate schools?
2. Abingdon
A small town in the Blue Ridge Mountains with the Virginia Creeper Trail, Abingdon is one of the best places to go for nature lovers and people who are fascinated with American history.
Besides the trail, this town with a few thousand people boasts a historic downtown area with a stunning arts and culture scene.
Did you know that Abingdon is 133 miles away from the popular city, of Roanoke? This town is best known for its outdoor activities but also for its influences on music.
To dive deeper into the local music scene, stop by The Crooked Road: Virginia’s Heritage Music Trail.
Historical Things to Do in Abingdon
- Barter Theatre
- William King Art Museum
- Abingdon Vineyards
- Arts Depot
- Fields-Penn 1860 House Museum
3. Chincoteague
Even though Chincoteague brings in a fair amount of crowds during the warm season, it is quite the hidden gem in Virginia.
The small beach town not only makes you feel like you’re on a getaway but you get to see wild ponies as well!
While you’re in Chincoteague, visit the museum that tells you more about the town.
After soaking in the history of Chincoteague, it’s time to go to the stunning Assateague Lighthouse.
Even though Chincoteague Island does have commercialized hotels, there are still plenty of beach-inspired airbnbs and homes for low prices.
Places to Stay in Chincoteague
- Chincoteague Island Tranquil Shores
- Beautiful Bayfront
- Key West Cottages
Things to do in Chincoteague
- Go shopping at the local shops (Sundial Books and Blue Crab Treasures)
- Visit the Refuge Waterfowl Museum and Waterman Memorial
- Take home fresh produce and gifts at the Farmers and Artisans Market
- Marvel at the local art scene by visiting Osprey Nest Art Gallery
- Surfside Golf
4. Woodstock
A small town in Shenandoah County, Woodstock is a town that not a lot of people know about compared to some of the others on this list.
The most popular attractions in Woodstock are the wineries and the Woodstock Museum. Other than the museum and vineyards, W.O. Riley Park is a place to plan the perfect picnic.
You can also dine at Spring House Tavern, Paisano’s Italian Restaurant, and Woodstock Cafe.
Best Things to Do
- Have a drink at the Woodstock Brew House
- Spend the day painting at The Art Spot
- Explore the Grand Caverns and Big Schloss Mountain Peak
5. Cape Charles
Cape Charles is near the entrance of the Chesapeake Bay and on the Eastern Shore much like Chincoteague Island.
In this small town, there is a beach, cute boutiques, and even the world’s most Instagrammable bookshop.
While this town is mainly known for its coastal atmosphere and landscapes, there are quite a few historical landmarks to check out.
Things to do in Cape Charles
- Cape Charles Natural Area Preserve
- Explore Eyre Hall and the Tomb of Custis
- Kiptopeke Beach
- Cape Charles Historic District
- Visit Lemon Tree Gallery and Studio
- Cape Charles Fishing Pier
6. Fincastle
Even though Fincastle is located in the lesser-known Botetourt County, the town of less than a thousand is best appreciated for its American architecture.
The town was originally settled by Scotch-Irish and German immigrants from Pennsylvania in the 18th century. This underrated small town in Virginia grew into an important place for commerce, shops, and hotels.
Did you know that Fincastle was named after the last royal governor, Lord Fincastle?
Things to do in Fincastle
- Virginia Mountain Vineyards
- Little Critters Traveling Petting Zoo
- Botetourt County and Historical Society and Museum
- Visit the Heritage Family Market
- Watch a play at the Attic Productions
7. Warrenton
Warrenton is also a town that no one ever talks about but is home to awesome attractions. If you’re a big fan of nature, Warrenton offers some of the best places to spend time outdoors.
Back in the 19th century, Warrenton was also a resort destination for travelers coming from Richmond and Washington.
The charming and historic structures throughout this town make this place feel like you’re back in time.
Did you know that Warrenton is known as the horse county due to Virginia hosting the gold cup race here?
Things to do in Warrenton
- Lake Brittle
- Rady Park
- The Fauquier History Museum
- Warrenton Branch Greenway
- Pearmund Cellars
8. Damascus
This small town in Washington County is known as the Trail Town USA because seven trails in Virginia meet up to form an intersection including the Virginia Creeper Trail.
Don’t confuse Damascus for the city in Syria. The small town is surely one to hit for all nature lovers.
There’s even a restaurant named 7 Trails Grill for local cuisine.
The town also hosts an annual Trail Days festival to support people serving in the event with a ton more activities to keep every visitor busy including raffles, pageants, and live music.
Things to Do
- Visit Downtown Damascus for colorful murals
- Explore Backbone Rock (a stone of Holston Mountain)
- Visit the Damascus Brewery & Tap Room
- Take a self-guided history tour
9. Floyd
Along with Fincastle, Floyd is a small town in the Roanoke Valley. What makes this Virginia town stand out among the others is its appreciation for music and the arts.
The small town is also known for its natural beauty with numerous shops, galleries, and hand-crafted gifts.
At the Floyd County Store, there is an opportunity to see some of the best musicians in the country.
You can’t forget to check out Bluegrass on Sundays!
Things to do in Floyd
- Floyd Center for the Arts
- Mabry Mill
- Floyd Farmer’s Market
- Chateau Morrisette (Virginia’s largest winery)
- Blue Ridge Parkway
- Floyd County Historical Society Museum
10. Onancock
A gem of Virginia’s eastern shore, Onancock is home to charming Victorian-style houses and boutiques.
Once you’ve soaked in the beauty of Onancock, take a ferry out to Tangier Island for a true getaway. Even though Onancock is a small town in Virginia, there are still quite a few things to do here.
For those who want a unique experience, cruise or paddle down Onancock Creek and catch the sunset.
While this town has chain hotels like Holiday Inn, to dive deeper into the local culture, consider staying in one of the beautiful inns or bed & breakfasts like The Inn at Onancock, 1882 Colonial Manor, or the Spinning Wheel Bed & Breakfast.
Things to do in Onancock
- Burnham Guides Paddling Adventures
- Crockett Gallery
- North Street Playhouse
- Danny Doughty Gallery
- The Blarney Stone Pub
- Burnham Guides Paddle & Bike
Many of these small towns are relatively close to each other and make a great extended road trip to learn more about Virginia’s history, nature, and cultural scene.
I can definitely say that you won’t be disappointed in the mountain views and natural landscapes.
Whether you enjoy the arts or are just a history buff, these small towns in Virginia are worth visiting.
The great part about each town is there are enough things to do for an enriching weekend stay.
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