The backroads of Americana music crisscross Southwest Virginia, from Rocky Mount to Pennington Gap. Virginia’s Heritage Music Trail—the Crooked Road—winds through Appalachia and leads from venue to festival, to the birthplace of country music and past homes of legends who forged a sound by blending gospel, African rhythms, and Western European folk traditions. In the late 18th century, immigrants from Ireland, England, and Germany arrived in the “new lands” of North America. Africans had arrived on slave ships almost two centuries earlier. Eventually, the newcomers spread into the mountainous west. The convergence of customs, especially in music, blended to create a unique Appalachian identity.
Referred to as the Traditional Appalachian Music period, music from the 1700s to early 1900s passed from player to player. Ballads were oral traditions, and instrumental tunes encouraged dancing. Also at this time, Europeans introduced the fiddle to American music. Africans brought the banjo, fashioning gourds into replicas of their native lutes (called akonting and ngoni).
As the nation grew, historians recognized the importance of cataloging American culture. Old-time music evolved as a respected genre that included the rich sounds of Southwest Virginia. In this new era, Appalachian music spread by radio, and in 1927 via the recorded disk. The Bristol Sessions, which included performances by A. P., Sara, and Maybelle Carter from Maces Spring in Scott County, fully captured the rhythms of old-time music. It was the “big bang” of country music—quickly, the Carters became the genre’s First Family.
The physical migration of Appalachian music runs veins through every hollow and hillside of the Commonwealth. But its roots are deepest in Southwest Virginia. In 2004, Virginia’s musicians, public officials, and citizens in general searched for a way to showcase this musical heritage. The Crooked Road, a driving trail connecting venues, historic sights, and memorable places of Appalachian music history, was born.
For more than 22 years, the 330-mile road has grown into a cultural statement, a living testament to the past, and a titan of preservation. Even Eleanor Roosevelt attempted to preserve a bit of the trail before it existed; a fact visitors can learn more about on their travels through Southwest Virginia. This primer will get you rolling through the 19 counties along the Crooked Road.
Major Venues
Carter Family Fold, Hiltons
Tucked into the hillside of Clinch Mountain, this legendary venue keeps the spirit of the “First Family of Country Music” alive. Today, the 800-seat venue—run by Rita Forrester, Janette Carter’s daughter—hosts bluegrass, folk, and country performances year-round.
Rex Theatre, Galax
Every Friday night, WBRF Classic Country 98.1 listeners tune in to hear Blue Ridge Backroads Live from the Rex. Upcoming acts include Becky Buller, the Jeff Little Trio, and The Broken Hearts. Originally opened in 1940 as the area’s first movie house, the City of Galax restored this 475-seat gem in the ’90s, and it now anchors Historic Downtown. Don’t miss the free movies every Wednesday.
SIDE STOP: Creek Bottom Brewing Co.
A burger of the month, a selection of standard and seasonal beers, and live, local music make Creek Bottom a popular spot for Crooked Road travelers.
307 N. Meadow St., Galax
Other Major Venues
Southwest Virginia Cultural Center & Marketplace, Abingdon
Country Cabin II, Norton
Blue Ridge Music Center, Galax
Affiliated Venues
Big Walker Lookout, Wytheville
Back when roadside attractions reigned, Stuart Kime built a 100-foot observation tower atop Big Walker Mountain. Since 1947, travelers along the scenic byway stop to marvel at sweeping vistas of patchwork farms and spectacular views of the Jefferson National Forest. From May–October, the family-run country store doubles as a music venue, hosting free Mountain Top Music concerts by local artists.
SIDE STOP: Skeeter’s
After visiting Big Walker Lookout, swing into downtown Wytheville to grab a hot dog at Skeeter’s, a lunch counter lovingly stuck in the ’50s.
165 E. Main St., Wytheville
Lincoln Theatre, Marion
With its rare Mayan Revival architecture, the Lincoln Theatre is a showstopper
even before the curtain rises. It is the filming site for Song of the Mountains, “the official TV series of Virginia,” which features bluegrass, Americana, and old-time legends like Steve Earle and Lorrie Morgan. Airing nationwide, the series invites travelers to catch a live taping the first Saturday of each month.
SIDE STOP: Better Coffee Co.
After a night at the Lincoln Theater, get a pick-me-up at Better Coffee Co., known
for their nitro creations and seriously good donuts.
111 Broad St., Marion
Other Affiliated Venues
Lays Hardware Center for the Arts, Coeburn
Lloyd’s Barber Shop and Banjo Museum, Rural Retreat
Blacksburg Market Square Park, Blacksburg
The Historic 1908 Courthouse, Independence
Festivals
Bristol Rhythm & Roots Reunion, Bristol
This is the big one. Each September, tens of thousands flood the twin cities of Bristol for a three-day celebration of roots, rhythm, and everything in between.
FloydFest, Check
Flatfooters pack the Floyd Country Store year-round for Friday night jams, but July belongs to FloydFest. This five-day fest blends southern rock, bluegrass, and global grooves—from southern rockers Gov’t Mule to the Afro-Cuban Grammy nominee Cimafunk. Camp under the stars, glamp in comfort, or park your RV. The family-friendly fest keeps little ones entertained with the Children’s Universe.
Old Fiddlers Convention, Galax
Galax is the modern epicenter of roots music, and since 1935 the Old Fiddlers Convention has summoned toe-tappers to this small town near the North Carolina border. Hundreds come to pick, bow, and sing, from fresh-faced fiddlers to veteran bluegrass bands. No amps allowed, anywhere. Camping is first-come, first-served, and run by the Galax Moose Lodge.
Museums
Birthplace of Country Music Museum, Bristol
In 1927, the Bristol Sessions changed the recording industry—and this Smithsonian-affiliated museum tells the story. Interactive displays, rare recordings, and a working radio station bring the history of country music to life. Monthly speaker series, concerts, and special exhibits keep it fresh.
“These recordings in Bristol in 1927 are the single most important event in the history of country music.” —Johnny Cash
SIDE STOP: Union 41
Celebrity Chef Torrece ‘Chef T’ Gregoire (Hell’s Kitchen, Big Restaurant Bet, Yes, Chef!) made a home in Bristol by adapting a circa 1930s bus station into a culinary experience.
171 Piedmont Ave., Bristol
Ralph Stanley Museum, Clintwood
Ralph Stanley is bluegrass. Just 8 miles from his birthplace, this museum charts his life from Appalachian roots to global fame. Two floors of photos, instruments, and stories trace Stanley’s legacy, including his Grammy for “O Death” from the movie O Brother, Where Art Thou? The museum also partners with the Jettie Baker Center to bring live music to Main Street Clintwood.
Other Museums and Centers:
The Blue Ridge Institute and Farm Museum, Ferrum
Wayne C. Henderson School of Appalachian Arts, Marion
Southwest Virginia Museum State Park, Big Stone Gap
Featured photo of Mt. Joy performing at FloydFest 2025 by Lexi Simcic. This article originally appeared in the December 2025 issue.
