10 Must-Visit Small Towns in Virginia

Are you looking for the best small towns in Virginia to visit or vacation? Check out our list of favorite small towns, with things to do, in Virginia!

The Commonwealth of Virginia is sprinkled with 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!

#1 – Town of Smithfield, Virginia

The small, charming Town of Smithfield, Virginia, 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.

Isle of Wight County Museum

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

Windsor Castle Park

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

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

Where to Eat in Smithfield

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’re looking for 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.

#2 – Town of Cape Charles, Virginia

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

Cape Charles Historic District

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

Outdoor Activities

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

#3 – Town of Chincoteague, Virginia

The Town of Chincoteague is a quaint small town located on Virginia’s Eastern Shore. The town is famous for the Chincoteague Island Pony Swim which thousands of people attend each year. And in addition to beautiful beaches, Chincoteague offers lots of things to do outdoors!

Chincoteague Island Pony Swim

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

Outdoor Activities

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 over 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.

#4 – 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 pf a college town. The Town of Farmville is also known for its rich history and outdoor activity options.

Things to Do in Farmville

When visiting Farmville, you’ll want to start on Main Street. Grab a cup of coffee and a bite to eat at the Uptown Coffee Café, a local favorite. Then, head over 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!

Outdoor Activities in Farmville

Are you looking to get outside? Farmville has several great outdoor activity options! Check out the Adventure Park at Sandy River Retreat and go zip lining or try out 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, if you’re interested in canoeing, kayaking, fishing, or boating Bear Creek Lake State Park is a great option.

#5 – Town of Ashland, Virginia

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

Things to do in Ashland

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.

Grab a Bite to Eat

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 to hang out at Andy’s and play pool or listen 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!

#6 – Town of Culpeper, Virginia

The Town of Culpeper is a larger small town coming in at 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.

Things to Do in Culpeper

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


If you’re looking to get outdoors, embark on an agrotourism journey and support a local farm! Or head over to Lake Pelham Adventures and 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.

Wineries and Breweries

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. However, if you’re looking for beer options, Beer Hound Brewery or Far Gohn Brewing Company are two excellent choices.

#7 – Town of Blacksburg, Virginia

A college town nestled 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 a host of other outdoor activities.

Virginia Polytechnic Institute and State University

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.   

Other Things To Do in Blacksburg, VA

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

#8 – Town of Abingdon, Virginia

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

Historic Main Street

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. While the Market District is where you’ll find the Farmer’s Market, dining, and more shopping.  

Other Things To Do in Abingdon, VA

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

#9 – Town of Leesburg, Virginia

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, VA

  • 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

Leesburg’s Arts and Culture District

The Arts and Culture District is a place for 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.

#10 – Town of Luray, Virginia

Situated in Virginia’s Shenandoah Valley, the small Town of Luray, Virginia, was founded in 1812. While the population size of this town is relatively small, surprisingly, there are lots of exciting things to do in Luray. This small Virginia town has a lot to offer, from caverns and wineries to national parks and scenic drives.

Luray Caverns

Visiting the Luray Caverns is perhaps the top thing to do in Luray and the surrounding 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. There is a Garden Maze and Adventure Park for which you can also purchase tickets.  

Other Things To Do in Luray

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, go camping, experience waterfalls, go on a scenic drive down Skyline Drive, and more. And if the kids need something to do, take them to an adventure park, go ziplining, or visit the Luray Zoo.

10 Must-Visit Small Towns in Virginia
Alexandrea Sumuel

Alexandrea Sumuel is a travel writer and the founder of Wander With Alex, where she provides vacationers and travel enthusiasts with trip ideas, travel guides, news, and itineraries. She travels to experience, eat, and explore-- and, on occasion, escape! Alex’s mission is to help people travel a little easier.