Ultimate Road Trip in America: A Music Lover’s Dream Through the Stunning Mountains of Virginia

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Floyd Country Store on the Crooked Road

Nestled within the Appalachian Mountain range in Southwest Virginia, music enthusiasts will find a one-of-a-kind road trip along what’s called the Crooked Road. While traveling the route, you’ll be able to walk in the footsteps of musical legends and experience America’s musical heritage through the sounds of bluegrass, gospel, old-time, folk, country, blues, and a variety of other genres.



The Crooked Road, also called Virginia’s Heritage Music Trail, was first conceptualized in 2003 and stretches 333 miles. It received an outpouring of support from local communities, venues, and musicians at its inception, and it now attracts travelers from around the world, generating millions of dollars in tourism revenue each year. The scenic route through the Blue Ridge Mountains allows you to enjoy beautiful natural views and plenty of charming small towns. 

In fact, the road passes through more than 50 towns, all with unique musical attractions. Historic theaters, outdoor venues, concert halls, and seasonal festivals offer travelers multiple places to tap their toes and listen to some of the country’s top musicians and local bands. If you want to experience the heart and soul of traditional Americana music and culture, pack your bags and hit The Crooked Road for an unforgettable vacation.

Venues, festivals, and music history

Dancers at a musical performance

The Crooked Road features 11 major venues and more than 60 affiliate venues that highlight the region’s musical heritage through live music performances, museum exhibitions, and cultural events. The major venues along the route include The Blue Ridge Music Center, The Birthplace of Country Music Museum, and The Rex Theater, among others. 



Whatever you do, don’t skip a stop at the iconic Floyd Country Store, a major venue on the Crooked Road. Operating as a country store during the day, it transforms into a lively celebration of traditional Southern Appalachian music and dance during the Friday Night Jamboree and the Sunday jam. Additionally, the Carter Family Fold, a barn-like 800-person music venue along the route, has live music every Saturday night and was the last place the legendary Johnny Cash ever performed live.

If your timing is flexible, consider planning your trip around one of the many music festivals along The Crooked Road. There’s something for everyone, from small festivals featuring local musicians to large-scale productions with multiple stages. FloydFest is an annual event held in July with a lineup that blends genres from around the world, including bluegrass, folk, rock, reggae, and more. Keep an eye on the Crooked Road website for a full list of events.

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In addition to the wonderful music, carve out some time in your itinerary to enjoy the region’s shopping. Browse through the local antique stores, art galleries, and boutiques selling locally-made crafts — you may find one-of-a-kind treasures to commemorate your trip. 



Planning your trip

Bristol signage

The Crooked Road mostly runs along U.S. Route 58. To make the most of the region’s music, history, and natural beauty, it is best to budget for at least four days, but you can stretch the trip for as long as you’d like. It’s an excellent route for those traveling through the United States in an RV or camper van. There are state park campgrounds and RV parks located along the way, making it easy to plan a successful RV trip. 

You can begin the road trip from either direction, east or west. If you want to start from the east, begin in Rocky Mount. Known as the Moonshine Capital of the World, Rocky Mount is full of distilleries and is home to the Blue Ridge Folklife Festival. If you’re starting on the western end, begin in Bristol, where you’ll find the Birthplace of Country Music Museum.

For a romantic experience, stay in some boutique hotels and family-owned bed and breakfasts during your road trip. The Bristol Hotel has been rated one of the top hotels in the United States and makes an excellent home base on the eastern part of the trip. Hit up the rooftop bar for happy hour and enjoy breathtaking views of the Appalachian Mountains. Rooms start at around $150 per night. The Martha Washington Inn and Spa is another excellent choice. With historic charm, gorgeous grounds, and luxurious spa treatments, it’s the perfect choice for a romantic getaway. 

Dave Pennells

By Dave Pennells

Dave Pennells, MS, has contributed his expertise as a career consultant and training specialist across various fields for over 15 years. At City University of Seattle, he offers personal career counseling and conducts workshops focused on practical job search techniques, resume creation, and interview skills. With a Master of Science in Counseling, Pennells specializes in career consulting, conducting career assessments, guiding career transitions, and providing outplacement services. Her professional experience spans multiple sectors, including banking, retail, airlines, non-profit organizations, and the aerospace industry. Additionally, since 2001, he has been actively involved with the Career Development Association of Australia.