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The Crooked Road: Two-wheeling and Two-Stepping Across Virginia’s Heritage Music Trail

September 12, 2025 by Pamela Collins

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Like mashed potatoes and gravy, road trips and music just belong together. Either alone is fine, but the pairing makes a memorable, comforting combination, better together than separately.

But better yet, now imagine the road and the music and you on two-wheels, with a real-time, real-life musical soundtrack underscoring your ride.

Welcome to Virginia’s “Crooked Road,” the ultimate musical road trip. Music — quite literally — accompanies all who journey this 333-mile stretch of Virginia Heritage Highway. As you cross it, listen — you’ll hear the history of American music singing from its hills, hollows and farms, musical tales of lives and struggles as twisty and sharp as the path of its roads. And you’ll learn how today’s country music mega-superstars owe much to this region, acknowledged as the birthplace of modern-day country, bluegrass, and mountain music.

The country music industry began here — the first country-music recordings, the first country music stars, the first country-music radio show all started along The Crooked Road. And, like a perennial bumper crop nourished by continually fertile soil, its musical tradition thrives still. The sound of music indeed lives in these hills and valleys, whether in the stripped starkness of western Virginia’s coal towns or the homespun neighborliness of its tiny Blue Ridge Mountain burgs.

Prepare for a history lesson unlike any other when riding The Crooked Road. No books, no manuals, just listen. A diner here, a street corner there, the country store up the road, the dance hall down the street, everywhere people don’t just perform, they jam. Here, the music plays hostess duties, introducing guests to each other like at a grand party.

Technically, one highway doesn’t comprise The Crooked Road, rather a series of roads link together to form the route. This primarily east-west running corridor lives up to its name of “crooked,” with tight, technical twisties in some areas and grand, scenic sweepers in others, all on mainly-traffic free two-lane roads. Along the way sights vary from pastoral farms to craggy mountain crests and panoramic, “wow”-producing views. The Blue Ridge Parkway — check. Virginia’s tallest mountain — check. Norman Rockwell-esque towns — check.

Rocky Mount, Virginia, just southeast of Roanoke, serves as the Crooked Road’s eastern gateway. Lodging and restaurants populate this quaint city that serves as a pleasant starting point for the journey.

The Crooked Road tells its story using a variety of multi-dimensional, entertaining methods that begin soon after leaving Rocky Mount. First, keep your eyes sharp for the periodic Wayside Exhibits that line the route end to end. These sometime highlight facts about the terrain you see, the places you are, and, most commonly, the music and the music-makers from the surrounding locales. Some even “play” music or interviews when you press their buttons.

Other exhibits stand large-as-life, such as theatres, dance halls, and venues. The first you’ll meet traveling eastward is the Crooked Road display at the Blue Ridge Institute and Museum at Ferrum College, just west of Rocky Mount. Here, a comprehensive exhibit discusses the Crooked Road’s musicians, heritage, and unique significance to American cultural history. The museum details how European music emigrated here, set root in this region and, fertilized with hard work and watered with simple joys, grew into the contemporary melodies and harmonies practiced today.

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Moonshine and music

Following this introduction, continue west on Route 40 for a bit then turn right for a ride into a salacious bite of local lore. Fulton County’s notorious, more gossip-worthy claim to fame lies as Moonshine Capital of Virginia, and Shooting Star Road that you’re now riding was a popular trade route for local bootleggers trying to evade the “revenuers.” Traveling it north into the mountains you can experience their same challenges, trying not to fly off the narrow zig-zig of road into the deep-lying gullies lining every turn. For those of us with legal cargo, we can scrub some speed and enjoy the curvy ride over this mountain road that leads toward Floyd.

Welcome to one of the major stops on the Crooked Road, and if at all possible, schedule your ride to stop in Floyd on a Friday night. Then listen: The music attracts like the Pied Piper, sounding from all directions. From the Floyd General Store, where folks pack the floor like countrified sardines in a dance hall can. Hear it from that downtown corner, where a harmonica and guitar player just joined a fiddler. It sounds from the park, where another group just started jamming together on the classic tune Cotton-Eyed Joe. Martha and her Vandellas would heartily approve of the “dancing in the streets” in this mountain town on Friday nights.

From Floyd, return to the Crooked Road via Route — 8, a lovely stretch of curvy blacktop that gracefully snakes back over the Blue Ridge Parkway, leading down to a beautiful valley bounded by forested hills and emerald fields.

Heading west again on Route 58, enjoy the energetic twisties that lead you to the locally famous “Lover’s Leap” overlook, offering sweeping views of the valley some 3,800 feet below. Soon you’ll cross the Blue Ridge Parkway again near Meadows of Dan, and ride into Hillsville, home to various lodging choices and not far from Floyd, about 26 miles via Route 221 and convenient for taking in those previously mentioned Friday night festivities.

Music in them hills

Traveling west from Hillsville, make for picturesque Galax, the “World Capital of Old-Time Mountain Music.” In true Americana-style, flags sway from the light poles lining the main route as if two-stepping to the fiddle music for which Galax is famous. On Grayson Street lives the neon-lit Rex Theater, still introducing local musicians to new audiences every Friday night. Galax also hosts the annual Old Fiddler’s Convention, a competitive tradition that began in 1935.

The Barter Theatre.

Return to traveling westward on Route 58. Now the Crooked Road winds through southernmost Virginia, skimming the border shared with North Carolina. The ups and downs, rights and lefts here give credence to this musical road’s name, sometimes soaring, sometimes dropping, always entertaining and smile-inducing … like a favorite bluegrass song.

Now you’ll travel through Grayson County, passing five of Virginia’s highest mountains on twisty Route 58, including Mount Rogers, its elevation stretching to 5,700 feet. From here you begin a fun trek downhill into a cooling shaded valley where the road mimics the tight turns of resident gurgling creeks.

Route 58 leads to Interstate 81. Travel southward for a bit, and then take the exit for Abingdon, a larger though genteel town along The Crooked Road offering a variety of lodging options. Make sure to visit the city’s Historic District, its picturesque parks, the stately Martha Washington Hotel & Spa, and maybe take in a show at the Barter Theater. Its owner charged 40 cents or “the equivalent amount in produce” to see live entertainment when it opened in 1933, begetting its name The Barter Theater. Now this handsome landmark, the nation’s longest running professional theater, entertains upwards of 160,000 people each year, though vegetables won’t get you in the door anymore.

The Martha Washington Hotel.

Another don’t miss stop near Abingdon is the Southwest Virginia Cultural Center and Marketplace (formerly known as Heartwood), just a few short miles south on Interstate 81. This beautiful facility is billed as “Southwest Virginia’s Artisan Gateway,” and offers locally handcrafted items, foods and wines for purchase, as well as its own restaurant featuring locally sourced foods. Virginia’s Crooked Road history, music, and instruments receive their own dedicated, detailed exhibit here.

Bristol, the birthplace

The Crooked Road’s next stop is Bristol, and depending where you stand, you’ll find yourself either in Virginia or Tennessee, for it straddles both borders. Most experts admit that commercial country music began here, and this city proudly wears the title of “Birthplace of County Music.”

The story’s short version goes that in 1927 a Victor Talking Machine Company representative set up a portable studio on State Street, recording 27 songs by 19 different acts, including the Carter Family and Jimmie Rodgers. Those records stoked the flames and popularity of this home-grown music, which led to more recordings and even a national radio show. None other than Johnny Cash (who married into the legendary Carter family) called the Bristol Sessions the “single most important event in the history of country music.”

Congress bestowed Bristol with the official Birthplace of Country Music designation in 1998. These sessions unleashed this musical genre from its country and mountain borders and played it for the world.

The Birthplace of Country Music Alliance in Bristol, a museum, details the white-lightening-like growth of the music genre as well as the lives of some of its earliest performers.

Music in the valley

Return to Route 58 West and enjoy the rolling slideshow of picturesque scenes painting its corners. And, if it’s Saturday night, follow your ears. Listen for the fiddlin’, the picking and the clogging that punctuate this pretty green valley, for the sound and spirit here at the Carter Family Fold will out-roar any motorcycle exhaust. Prepare yourself, for inside this rustic music theater bellows the sounds of simple joys — only acoustic instruments allowed. Babies in strollers, grannies with walkers, whether wearing the latest in leather-tooled cowboy boots or just-in-from-the-field dungarees, the dress code is simple: wear your smile.

The theater sits as part of the larger Carter Family Memorial Music Center, established to honor and preserve the music of the original Carter Family who recorded those 1927 Bristol Sessions. The Carter Family Museum (originally A.P. Carter’s former general store) documents the history of the “first family of country music.” A.P. Carter, wife Sara, and her cousin Maybelle lived here at Clinch Mountain’s foot in Poor Valley.

Westward travel on Route 58 soon turns northward onto Routes 23, 83 and 80 as The Crooked Road fishhooks upward. The landscape loses it pastoral lushness as it changes to grayer crags and mountainsides. This is western Virginia coal country now, scrappy but resilient, stubborn as the rock from which it’s hewn. Music from here reflects this harshness but sings of hope, a necessary combination. The Ralph Stanley Museum and Traditional Mountain Music Center in Clintwood warrants a side trip. The three-time Grammy Award winning artist is lauded for his contribution to performing and preserving traditional Southwest Virginia “mountain music.” He earned his largest audience from the movie “Oh Brother, Where Art Thou,” that featured his music.

The Crooked Road ends, befittingly, after about a 15-mile section of narrow, winding, crooked twisties that take you to Breaks Interstate State Park, called the “Grand Canyon of the South.” Located at the Virginia-Kentucky border, it boasts a five-mile-long canyon that plunges over 1,650 feet.

 “The Crooked Road.” From the moment it seductively sang its siren’s call destiny intervened, for what self-respecting motorcyclist could ignore a name that’s music to our ears? Turns out, the Crooked Road gives riders plenty of entertainment — musical and otherwise — with its ribbons of its twisty tarmac and its asphalt-paved, fiddle-tinged, real-life music and history lesson about America’s harmonious heritage. 

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Filed Under: Rider Tours Tagged With: abingdon, adventure, appalachian, art, arts, barter theatre, birthplace of country music, blue ridge institute and museum, bristol, carter family, carter family fold, country music, crooked road, culture, duo ride, ferrum college, Floyd, floyd general store, galax, grayson county, history, journey, live music, mount rogers, music, Old Fiddler’s Convention, rocky mount, Tennessee, Virginia, virginia heritage highway

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