Small Towns in Virginia Waiting to be Discovered

The Commonwealth of Virginia has historic, charming, picturesque, and tranquil small towns. Residents of these small towns cherish their little corner of Virginia and tend to feel a deep sense of community and cultural pride. Below, you’ll find a list of some of the best small towns in Virginia– with things to do!

Town of Smithfield, Virginia

Smithfield, Virginia (2)
Photo Credit: Alexandrea Sumuel

Smithfield, Virginia’s small, charming town, is in Isle of Wight County and is considered part of Hampton Roads. The town is about 45 minutes from Norfolk and an hour from Virginia Beach. Smithfield, VA, is home to the Fortune 500 company Smithfield Foods and is famous for the Smithfield Ham. Lovingly, the Town of Smithfield is often referred to as Hamtown.

Check out the Isle of Wight County Museum to learn more about Smithfield and the area. Learn about how the town came to be, and view the world’s oldest ham, peanut, etc. The museum also offers walking tours of Windsor Castle Park and Fort Boykin.

Windsor Castle Park is a beautiful riverside park in Smithfield that many locals enjoy. The park offers a dog park, fishing pier, kayak launch, bike path, and walking trails.

Windsor Castle Park is also home to many of Smithfield’s festivals, including the Bacon Bourbon Fest, Wine and Brew Fest, and the BOB Fest (Brunswick Stew, Oysters, and BBQ). 

You’ll want to grab a bite to eat when you’re in town. You can’t go wrong with the Cockeyed Rooster if you want breakfast. Check out the Smithfield Inn for a fried green tomato BLT or a bowl of shrimp and grits for lunch. Come dinner time, head over to the Smithfield Station for a meal on the water or Wharfhill for a good brew.

Town of Cape Charles, Virginia

Cape Charles Beach
Photo Credit: Alexandrea Sumuel

Cape Charles is a quaint small town on Virginia’s Eastern Shore. It is a beach town with access to the shores of the Chesapeake Bay. Incorporated in 1886, the current population is around one thousand.

Start your day by exploring the Cape Charles Historic District! The historic district offers dining, shopping, and entertainment options. Stop by The Bakery on Mason for a made-from-scratch breakfast pastry. Swing by the Cape Charles Coffeehouse for an excellent cup of coffee. Visit the Historic Palace Theatre for a show or shop at the local boutiques. Many locals and visitors rent golf carts to get around town.

If you’re looking for outdoor activities, head to Cape Charles Beach for a bit of sunbathing, kayaking, or stand-up paddleboarding. You can also visit the Cape Charles Natural Area Preserve or Kiptopeke State Park for a great hike.  

Town of Chincoteague, Virginia

Chincoteague Wildlife Refuge in Virginia
Photo Credit: [@paulbradyphoto/DepositPhotos]

Chincoteague is a quaint small town on Virginia’s Eastern Shore. It is famous for the Chincoteague Island Pony Swim, which thousands attend yearly. In addition to beautiful beaches, Chincoteague offers many things to do outdoors!

Since 1925, wild ponies have been herded from Assateague Island to Chincoteague Island to be sold at auction. The ponies are herded by volunteer firefighters on horseback called the Saltwater Cowboys. The event is magnificent, and many people gather to watch the ponies swim across the water.

The Chincoteague National Wildlife Refuge is one of the top places to explore, offering beaches, wildlife, hiking, and biking. And if you’d rather be in or around the water, head to the Seaside Water Trail for kayaking and canoeing. Fishing is also a big deal in Chincoteague, so if you enjoy the activity, check out a fishing charter. Other outdoor activities include hunting, nature centers, eco-tours, boat cruises, and camping.

Town of Farmville, Virginia

Farmville, Virginia
Photo Credit: Town of Farmville, Virginia

The Town of Farmville is located in central Virginia, approximately an hour and fifteen minutes west of Richmond. The town is home to Longwood University and Hampton-Sydney College, making it somewhat of a college town. Farmville has a rich history and a wide range of outdoor activity options.

When visiting Farmville, you’ll want to start on Main Street. Grab a coffee and a bite at the Uptown Coffee Café, a local favorite. Then, head to the Robert Russa Monton Museum and learn about the area’s civil rights movement and the fight for equality. Finally, you’ll want to visit the Three Roads Brewing Company for a good brew, games, and live entertainment!

Check out the Adventure Park at Sandy River Retreat, zip lining, or try an obstacle course. If you’re looking for a great hike or bike ride, you’ll want to check out High Bridge Trail State Park. Lastly, Bear Creek Lake State Park is a great canoeing, kayaking, fishing, or boating option.

Town of Ashland, Virginia

Ashland, Virginia
Photo Credit: [@Dr Tom Photography/Shutterstock]

The town of Ashland, Virginia, is located approximately 20 minutes north of Richmond. Incorporated in 1858, it was initially developed by the railroad. Because of its central location in Virginia, locals refer to the town as the “Center of the Universe.” The Town is also home to the private liberal arts college of Randolph-Macon.

Start your visit with a trip to historic downtown Ashland. Visit the Ashland Museum & the Red Caboose to learn all about the town’s history. Then, take an Ashland haunted history or historic walking tour!  And if you’re a railroad fan, head over to the tracks to witness the large volume of freight and passenger trains come and go.

Check out Andy’s Restaurant and Lounge when you’re ready for a bite to eat. They’ve been serving quality homemade food since 1968! Many locals like hanging out at Andy’s, playing pool, or listening to live music. The Iron Horse Restaurant, which resides in a 100-year-old building, is another good dining option in Ashland. The Iron Horse serves brunch and has excellent customer service!

Town of Culpeper, Virginia

Culpeper, Virginia
Photo Credit: [@refrina/Shutterstock]

The Town of Culpeper is a larger small town with around twenty thousand people. Culpeper is in north-central Virginia and is situated at the eastern base of the Blue Ridge Mountains. The town offers numerous outdoor activities, art, history, culture, and agritourism.

Downtown Culpeper has many shops and dining options for you to choose from. The Flavor on Main is highly recommended if you want to grab a bite. The 1920s Art-Deco-themed restaurant is known for its great food and customer service. Next, to learn about the town’s history, head to the historic train depot and visit the Museum of Culpeper History. Finally, if you want something to do with friends, check out Puzzle Room Live, an escape room-style challenge. 

If you want to get outdoors, go on an agrotourism journey and support a local farm! Or head over to Lake Pelham Adventures, rent a canoe, kayak, paddleboard, or boat, and enjoy the Lake. Lastly, if you’re looking for a good hike, you’ll want to check out Yowell Meadow Park near downtown. There is a two-mile paved hiking trail, a nature trail, and a skate park.

The Town of Culpeper is home to a handful of wineries and breweries. Mountain Run Winery is known for its hospitality, great wine, and beautiful mountain views. Old House Vineyards is another excellent winery that was once an abandoned farmhouse. Beer Hound Brewery and Far Gohn Brewing Company are two excellent beer options.

Town of Blacksburg, Virginia

Blacksburg, Virginia
Photo Credit: [@Rui Serra Maia/Shutterstock]

A college town in southwest Virginia’s Blue Ridge Mountains, Blacksburg is home to the Virginia Tech Hokies. Blacksburg is part of the historic New River Valley (NRV), which provides opportunities for camping, fishing, kayaking, whitewater rafting, and other outdoor activities.

Virginia Tech has a significant presence in Blacksburg and is a huge economic driver. The college was one of the first universities in the area to offer agricultural engineering to its students. Virginia Tech football is a big deal on this campus and was quite successful during the many years of Coach Frank Beamer’s career. Fun fact: the school is said to have one of the loudest college stadiums in the country.   

If you want to learn more about Blacksburg’s establishment and history, check out the Alexander Black House and Cultural Center. Popular hiking spots include the Huckleberry Trail and the Deerfield Trail, and if you travel to the next county, you’ll have access to the Appalachian Trail. The Blacksburg Farmer’s Market, located downtown, is a great place to shop for local goods.

Town of Abingdon, Virginia

Another town in Southwest Virginia’s Blue Ridge Mountains, Abingdon, VA, is known for its outdoor activities and eclectic art scene.

Historic Main Street is where you’ll find dining, shopping, old buildings, art galleries, and more. Main Street comprises several districts, including Courthouse Hill, the Theatre District, and the Market District.

The Courthouse Hill district was revitalized in 2013 and is now home to many local shops. The Theatre District is home to the Barter Theatre and the historic Moonlight Drive-In. The Market District is where you’ll find the farmers’ market, dining, and more shopping.  

Outdoor enthusiasts can hike or bike the 35-mile Virginia Creeper Trail to the Town of Damascus. For the more adventurous, the Appalachian Trail is only 12 minutes from Abingdon. Finally, if you’re looking to learn more about Virginia wines, check out the Abingdon Vineyards.

Town of Leesburg, Virginia

Town of Leesburg, Virginia
Photo Credit: [@Nigel Jarvis/Shutterstock]

The historic Town of Leesburg, Virginia, is about an hour northwest of Washington, DC. The town was named after the ancestors of Robert E. Lee in the 1700s. Today, Leesburg can be found in Loudoun and holds the government seat for the county. Things to do in Leesburg include:

  • Oatlands Historic House and Gardens
  • George C. Marshall’s Dodona Manor
  • Ball’s Bluff Battlefield Regional Park
  • Visit the Lost Creek Vineyard and Winery
  • Hiking or Biking the W&OD Trail
  • Leesburg Animal Park

The Arts and Culture District allows local artists to express themselves. As an incentive for growth, the town offers many opportunities to artists willing to make the district their home. The district provides visitors with art galleries, live music, dining, and shopping.

Town of Luray, Virginia

The small town of Luray, founded in 1812, is situated in Virginia’s Shenandoah Valley. While its population is relatively small, surprisingly, there are lots of exciting things to do in Luray. This small Virginia town has much to offer, from caverns and wineries to national parks and scenic drives.

Visiting the Luray Caverns is perhaps the top thing to do in the area. Head underground and experience the natural wonders forming for over 4 million years. The caverns offer various formations such as columns, stalagmites, stalactites, and mirrored pools.

While you can take a self-guided tour, you should book a guided tour if you want more information on the cavern system. Other attractions included with your ticket are the Toy Town Junction, the Car and Carriage Museum, and the Shenandoah Heritage Village. You can also purchase tickets for a Garden Maze and Adventure Park.  

If you’re looking for a winery or distillery, check out Castle Vineyards, Faithbrooke Barn and Vineyards, or River Hill Distillery. Those wanting to get outdoors should take the short drive to Shenandoah National Park, where you can go hiking and camping, experience waterfalls, go on a scenic drive down Skyline Drive, and more. If the kids need something to do, take them to an adventure park, go ziplining, or visit the Luray Zoo.


Alexandrea Sumuel - Groves is a nationally syndicated travel writer and founder of the Wander With Alex travel blog. Her work has appeared on MSN, YAHOO!, Euronews, and FOX, ABC, and NBC affiliates across the United States. 

Alex travels to experience, eat, explore, and occasionally escape! She collaborates with destinations, vacation property management companies, and hospitality technology firms to provide her readers with exclusive insights and information.