Southwest Virginia Road Trip: Abingdon & the Crooked Road

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Are you a boomer traveler who can’t get enough of U.S. road trips? You’re in luck.

My Itchy Travel Feet featured writer, Debi Lander of ByLanderSea, introduces us to a road trip itinerary that’s perfect for touring Southwest Virginia. You’ll be amazed at the many things to do in Southwest Virginia!

‘Virginia is for Lovers’ ranks as one of the most successful tourism campaigns of all time. I personally know it’s been around for decades because I had a poster featuring the slogan on my college dorm wall. And, let’s just say I’m approaching my 50th college reunion!

The Old Dominion, however, entices more than romantics, from its seashores to its mountains, for its colonial and Civil War sites, its presidential mansions, and aerospace museums, not to mention many popular culinary and musical festivals. 

The word LOVE made out of sticks on the side of the road
Love Works at Big Walker Mountain

Where is Southwest Virginia?

Fall color at a Virginia winery
Abingdon Vineyards Tasting Room

Southwest Virginia, the westernmost tip of Virginia that stretches into the far left-hand side of the state map, includes the rugged Blue Ridge Mountains, part of the Appalachian chain. Driving time to the region takes about two hours from Asheville, NC, Knoxville, TN, and Roanoke, VA.

You’d need 4.5 hours if you’re coming from Nashville or Richmond or just minutes from Bristol, TN. Whatever direction, the state maintains good roads and highways, so it’s totally worth the drive.  

Exploring Abingdon on a Southwest Virginia Road Trip

Last fall, I enjoyed a Southwest Virginia road trip and discovered Abingdon, a sophisticated small city with fascinating history, old architectural gems, and modern activities. Abingdon kept me hopping over three days — not long enough to see and do it all. 

Attend a performance at the Barter Theater

Red brick building of Barter Theatre in Abindon, Virginia
Barter Theatre

Abingdon’s best known for the Barter Theatre that is also Virginia’s State Theater. The professional residential repertoire company, one of the few in the U.S., presents multiple stages, letting visitors see more than one performance over a weekend. 

The Barter began in the Great Depression when actors took vegetables locals couldn’t sell in exchange for entertainment. Milk, eggs, and livestock turned ham to Hamlet (vice versa for the equally struggling cast). It’s cash or credit cards today, but folks still leave in fine spirits. 

The best place to stay in Abingdon

Brick and white colonial building
The Martha Washington Inn

After a Barter performance, walk across the street to stay at, or at least visit the Martha Washington Inn and Spa. The historic hotel was originally built in 1935 as a residence for a large family.

Later the property became a school and, in 1935, a hotel. Explore the corridors and see its rich history through photos and memorabilia.

Today, “the Martha” maintains a colonial atmosphere that blends fine antiques with modern amenities. You’ll want to spend time there, not just sleep in your room.

Tables in a colonial era room covered with linen tablecloths, set for tea

The parlor begs for an afternoon tea service, and the library calls others to curl up and read. The manicured grounds make for a relaxing stroll, and don’t forget the indulging spa. 

Where to eat in Abingdon

Where to eat? Why, simply The Tavern, as its always been known since  1779. Dine surrounded by warm candlelight in a pub-like setting.

The Tavern stands as the oldest of the city’s historic buildings and home of Virginia’s oldest bar. The structure, originally constructed as a tavern and overnight inn for stagecoach travelers, welcomed famous guests such as Henry Clay; Louis Philippe, King of France; President Andrew Jackson; and Pierre Charles L’Enfant, designer of Washington D.C. 

The Tavern also served as a hospital for wounded Confederate and Union soldiers during the Civil War. If you are into ghosts, ask the owner to give you a peek in the attic.

The initials carved into the wall are real, but are the spirits? Abingdon’s Haint Mistress offers ghost tours of several properties and claims many specters are scattered about town. 

Stay active on the Virginia Creeper Trail

bicyclist riding on a wooden bridge of the Virginia Creeper Trail
Recreating on the Virginia Creeper Trail

Not far from the Tavern lies a scenic rails-to-trails path, the Virginia Creeper Trail, a popular outdoor Southwest Virginia attraction. The trail is ideal for biking, hiking, walking, or horseback riding. You can rent a cycle and hit the trails or ride over to the Abingdon Vineyards to quench your thirst.

As you’d expect, the vineyards host guests in a tasting room, but they also provide plenty of outdoor seating at picnic tables. Many locals bring their own blanket and sit a spell listening to live musicians. You’ll like meet the owners, an adorable young couple who moved from Napa to Abingdon to grow grapes and create wine. 

Learn about Abingdon early American history

cemetery surrounded by trees
Sinking Spring Cemetery

Some boomers like to roam among the centuries-old tombstones. Abingdon offers two historic cemeteries. The 11-acre Sinking Spring Cemetery was established as the burial ground for the Sinking Spring Presbyterian Church members back in 1773. 

On the same parcel of land, but separated by Russell Road, lies the burial place of the enslaved people owned by these early Presbyterians and free people of color. Pick up a brochure at the Visitors Center and take a self-guided walking tour of the cemetery.

For a more in-depth look at the local history, contact History Alive Tours. They’ll arrange for a living history guide for you. The historic character likely impersonating Lord Dunmore, the last colonial governor of Virginia, or Rev. Charles Cummings, The Fightin’ Parson, or Rufus Soule, tavern owner, will tell stories from their point of view. 

The Abingdon Muster Grounds, a site managed by the National Park Service, sits at the Overmountain Victory Trail’s northern trailhead. The patriot militia used the area during the American Revolution. The Interpretive Center explains the Battle of Kings Mountain and the Overmountain Victory, eye-opening history to me. 

Discover Appalachian arts

Art enthusiasts should head up the hill to the nationally accredited William King Museum. Here you’ll find decorative arts on display, stunning textiles, pottery, and furniture in the permanent collection.

I found the quilts and textiles very appealing. Changing art exhibits come and go to give returning guests something new. Note: admission is free.  

The old train station became home to the Arts Depot. Drop in to shop or see artists in residence working their crafts. The variety and quality are exceptional.  

Men playing string instruments at a folk center
Bluegrass performance

For a real treat, drive over to the Southwest Virginia Cultural Center,  a soaring glass, wood, and stone visitor center and gathering place showcasing the region’s music, crafts, and culture. Check the schedule for frequent free performances of bluegrass music.

Hold on to your wallet. This place will make you want to redecorate your house. From bedroom sets to tables, chairs, clocks, and quilts, top-of-the-line artisan crafts are displayed. I challenge you to leave without buying at least a small gift for someone.

The center also sells local Virginia specialties like smoked hams, peanuts, jams, pickles, and wine. I honestly have never been to a visitor center as spectacular as this one. 

Touring Southwest Virginia on a Crooked Road Tour

Old country store with rocking chairs on the front porch
General Store at Big Walker Mountain

Abingdon and the SWVA Cultural Center sit on The Crooked Road, a 300-mile trail dedicated to musical heritage. The trail winds through 19 counties, four cities, and over 50 towns.

It includes nine major venues and over 60 affiliated venues and festivals. Carrie Beck, director of the trail, says, “The venues and musicians of the region are truly unique and bring musical traditions to the visitors and their communities. It’s authenticity at its best.”

Stop along the way to hear the region’s distinctive music’s sounds and see the sights captured in various art forms by world-renowned folk artists. The Crooked Road highlights include:

  1. Blue Ridge Institute & Museum at Ferrum University – Ferrum
  2. Floyd Country Store – Floyd
  3. Blue Ridge Music Center – Galax
  4. Galax Old Fiddler’s Convention – Galax – first week in August
  5. Rex Theatre – Galax
  6. Southwest Virginia Cultural Center & Marketplace  – Abingdon
  7. Birthplace of Country Music – Bristol
  8. Carter Family Fold – Hiltons
  9. Country Cabin – Norton
  10. Ralph Stanley Museum – Clintwood

Discover Bristol, the birthplace of country music

If you saw Ken Burn’s documentary Country Music, you will be drawn to Bristol, the Birthplace of Country Music. Their museum tells the story of the famous groundbreaking ‘Sessions’ and explores how evolving sound technology led to the genre’s success. Through theater experiences, interactive displays, text, and artifacts, the surprising story of these recording sessions and their far-reaching influence come alive.  

The Carter Family was discovered in 1927 by Victor Recording Studio in Bristol and recorded 300 songs between 1927 and 1942. Playing traditional Appalachian music, the family became forerunners of our modern-day country music.

Janette Carter established the Carter Family Fold to honor her parents A.P. and Sara and Maybelle Carter’s memory. Now, her daughter Rita is carrying on the musical and performing legacy.

You can visit the Carter Family Fold at the foot of Clinch Mountain for programs of Old Time and bluegrass music on weekends. The Carter Fold is a rustic, 800+ seat music shed offering traditional music every Saturday. 

The Ralph Stanley Museum and Traditional Mountain Music Center features Stanley’s life and music, another pioneer in traditional Appalachian old-time music. Stanley donated his extensive collection of memorabilia – ranging from vintage instruments to countless musical awards – to the 2,200-square-foot museum. The facility acts as a resource center for students and music fans to learn more about traditional American and Appalachian music. 

Attend the Friday night Jamboree in Floyd

Traveling further along The Crooked Road, sooner or later, you will arrive at the two Towns of Floyd, which exist and occupy precisely the same geography.

There is the Floyd of the Back to the Land People who arrived about six decades ago. They came seeking to simplify their complicated lives by returning to the real values of country living. And there is the Floyd of today, yet with those who seem always to have been there.

Boomer Travel Tip

Looking for road trip tips and advice? Check out our U.S. road trip planner.

The place the two cultures come together is the Jamboree, an event that starts every Friday evening at the Floyd Country Store. When the weather is fine, the music of banjos, guitars, fiddles, and mandolins can be enjoyed up and down the street and on stage in The Country Store.

Flatfoot dancing, singing, and good foods are everywhere, like wood oven-baked pizza at Dog Town, coffee from the Red Rooster, and the lunch and dinner delights at Odd Fella’s Cafe.  Fine art and crafts are on display in many local shops. Don’t miss Floyd’s authentic spirit, the gathering of friendly people celebrating the magic of happiness itself. 

Experience the Claw of the Dragon

A road curving around a mountain top
The Claw of the Dragon

In central Southwest Virginia, you’ll discover a twisty and turny ride that’s unlike any other. I had the chance to drive just a small section of what is known as the Claw of the Dragon. I started in Wytheville and followed the pavement that runs through secluded, tree-filled scenery, exceptionally beautiful in the fall.

Wooden fire tower
Big Walker Lookout

My drive stopped at the top of Big Walker Mountain. Here I climbed Big Walker Lookout, a 100-foot observation platform with 360-degree views of the valley and picturesque farmscapes.

Sitting at the base lies a general store, a Crooked Road affiliated venue that sells hot dogs and ice cream, sundries, and  25+ artisans & crafters’ handmade works. This location features free, live concerts every Saturday and Sunday from May through October.

Once you tackle this part of the Dragon, it’s going to be almost impossible to stop you from wanting to see the rest. Be sure to venture into the Smoky Mountain Foothills of Tennessee to drive the Tail of the Dragon. It’s 11 miles of curvy fun that’s considered to be America’s number one motorcycle and sports car road.

I have no doubt that somewhere along your Virginia road trip, you’ll become lovers of Abingdon and the Crooked Road. 

Scratch those itchy travel feet!

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