7 Picturesque Small Towns To Visit In Virginia

There is something very special about Virginia — one of the original 13 colonies and a state with a wealth of history, rolling green hills, and traditions steeped like a perfect glass of sweet tea. Here are seven picturesque small towns to visit in Virginia that literally took my breath away. 

The towns (listed alphabetically) each have 25,000 or less in population and offer beauty and all the friendly hospitality that one would expect in the South.  

Note: I was hosted at Mimslyn Inn, Luray Caverns, and the Inn at Gristmill Square, but reviews are 100 percent my own opinion.

1. Abingdon 

Abingdon, Virginia, is home to the famous Barter Theatre and loads of small-town charm. Barter Theatre’s fall performances are at the Moonlite Theatre Drive-In, including Frankenstein and Rockin’ at the Moonlite. 

Abingdon is also on Virginia’s Crooked Road, a heritage music trail devoted to country music, bluegrass, music venues, and basically anything related to music. The Crooked Road runs 300 miles through the state. One of the most popular places is Abingdon’s Southwest Virginia Cultural Center & Marketplace, which also has crafts and food options. 

The Farmer’s market, local vineyards, and the William King Museum of Art are fun and trendy things to visit in Abingdon, or you might consider having a tasty craft beer at Wolf Hills Brewing Company.

Consider riding the Virginia Creeper Trail with gorgeous wooded and rustic landscapes if you have your bike. The picturesque trail is 34 miles long but not a hard ride so that you can ride it, or even parts of it, without being an avid cyclist. It is also part of the Rails to Trails project. 

Fun Fact: If you need to rent a bike, the Virginia Creeper Trail Bike Shop has rentals and a shuttle service. Helmets are included. 

2. Bristol 

A big draw in Bristol are the NASCAR races at the Bristol Motor Speedway, but Bristol is a city that straddles the state line, and that activity is on the Tennessee side. Bristol has a vibrant downtown area (namely State Street with 160 businesses) filled with neon-clad Paramount Center for the Arts art-deco theater, eye-catching murals, and a few enjoyable eateries. This fall, consider getting tickets to see Amy Grant, Trace Adkins, or Jefferson Starship. 

It is a leisurely stroll to see Bristol on foot, and parking is plentiful. You’ll also find the one-of-a-kind Birthplace of Country Music Museum, paying tribute to the 1927 Bristol Sessions where Jimmie Rodgers and many others recorded their first songs long before they were famous. 

The best thing about Bristol to me? Easy. The Blackbird Bakery in downtown Bristol is one of the best bakeries in the country, in my opinion. Aside from the lovely and delicious doughnuts, Blackbird has kolaches, fritters, banana pudding, cheesecakes, cupcakes, brownies, ice cream, and coffee. Your tastebuds are in for a real treat at this picturesque stop. Need more substance? Try the burgers and onion rings from Burger Bar right down the street. 

3. Gordonsville

Gordonsville was my home-away-from-home when I took my mom and aunt to visit Charlottesville. The drive is roughly 30 minutes away, but the scenery will keep you entertained and in awe the whole time. We stayed in a yurt at Shenandoah Crossing (Bluegreen timeshare property) with two bedrooms and rugged-chic decor. We all found it comfortable, original, and a super fun way to have a girls’ getaway. 

Gordonsville is best known for being the “Fried Chicken Capital of the World,” which is probably as shocking to you as it is to me. It has an appealing Main Street worth seeing. You’ll find a few galleries, antique shops, and trendy newer places for shopping that will fill your itinerary for a few good hours.

Consider lunch or dinner at Gordonsville’s Barbeque Exchange, a yummy restaurant with side dishes like broccoli salad, baked beans, and macaroni & cheese. And then, visit the Exchange Hotel Civil War Medical Museum and see if you have a ghost encounter. 

4. Lexington

I love the sheer number of historic sites and excellent museums in the town of Lexington. My favorite being the Stonewall Jackson House on the Virginia Military Institute property. Lexington was an important town during the Civil War, and memorabilia is found all around town. 

One of the most extraordinary things you can do here is taking a horse and carriage ride, but I prefer sampling the beer at Devils Backbone Brewing Company. You can also see a movie at the retro Hull’s Drive-In, an adorable retro venue that is one of only two nonprofit drive-ins in the country. 

Grab a salad, gourmet sandwiches (especially grilled cheese), burgers, or a hearty appetizer at Macado’s, serving pub-style food in a casual setting. For a more date night restaurant experience, Southern Inn Restaurant has white tablecloths, pimento cheese cheesecake, and a to-die-for New York strip.

Pro Tip: If you are into cemetery stops, you’ll find the gravesites of both generals Robert E. Lee and General Stonewall Jackson in Lexington. 

5. Luray

Luray rhymes with “hooray,” and that’s how you will feel when you discover it for the first time. When you drive into town, you will go down a hill with a picture-perfect small-town America downtown, complete with signs, flowers, and cute little locally-owned shops. Oh, and the stunning Blue Ridge Mountains as a backdrop. 

I recommend staying at the Mimslyn Inn, which has traditional hotel rooms or luxurious cottages to choose from. It has a fun and tasty speakeasy restaurant with live music that is just the right volume and a second restaurant in the lobby that serves enticing breakfast dishes. Luray is also the Cabin Capital of Virginia, so there are dozens of options for that type of overnight style. 

Luray is home to the Luray Caverns, well worth a visit, and accessible for all. I would allow an hour for the tour and then head over to see the museums next door. I rave about the car and toy museums often. 

Another fun stop that will scratch your nostalgia itch is Cooter’s, owned by Ben Jones, who played Cooter in the Dukes of Hazzard TV series. Ben is often at the fun-loving museum and tourist stop. 

Now, I’m going to let you in on a big secret. Gathering Grounds is a beloved downtown coffee shop, but the luscious slices of cakes and pies they make from scratch are even better than the delicious coffee drinks. I had a piece of the peach cake with spiced icing, which was life-changing.

Oh, and Luray is absolutely beautiful, with rolling mountains, river access for outdoor offerings, and the Shenandoah National Park, whose headquarters are in Luray. 

6. Staunton

I’m a presidential fan freak, so I nearly jumped out of the rolling car when my husband and I drove by the Woodrow Wilson Presidential Library and Museum. We ended up parking out back, so no harm done, and the museum was incredibly interesting and chock full of great exhibits. I loved the gift shop, too, with signature items and home accessories for entertaining and cute gift items. The Frontier Culture Museum is another great choice if you are a museum-goer. 

Staunton is a lovely, clean town, but it is hilly in parts. There are excellent restaurants, vineyards, breweries, and streets lined with gorgeous homes, galleries, and architecture. Any Shakespeare fans out there? Take in a live production of his famous works at the American Shakespeare Center, formerly the Blackfriars Playhouse. 

Consider staying at the newly renovated Hotel 24 South (formerly Stonewall Jackson Hotel) or one of the nine bed and breakfast accommodations.

7. Warm Springs

After stopping in the Virginia Visitors Center on my way to see my folks in West Virginia, I picked up a handful of travel brochures. Warm Springs was the one I fell in love with, and I scheduled a road trip there days later. Around 21 at the time, my youngest daughter went with me for three perfect days in the Warm/Hot springs area.

Some of the cool things we did were floating in the Jefferson Pools (or Warm Springs Pools), currently closed for renovations. We also grabbed picnic lunch items from Milk House Market and had a scenic picnic in a beautiful setting. We did not have a chance to see the Garth Newel Center, but it is a famous music venue that seems like a really great attraction. 

Peyton and I stayed at the Inn at Gristmill Square, with well-appointed rooms and the friendliest staff. Our room was on the first floor of the Steele House, which featured a dreamy soaking tub, separate shower area, and wood-burning fireplace. Breakfast was delivered to our door each morning via picnic basket and was out of this world! 

In nearby Hot Springs, you can opt for a more standard hotel setting at the Omni Homestead Resort, a hotel that 23 U.S. Presidents have stayed at through the years. Afternoon tea is a favorite activity at the Homestead, and the pools are amazing.