Highways · Crooked Road Caravan 2026
Our first Airstream Caravan is ten days along Virginia's Heritage Music Trail, chasing old-time and bluegrass music from a few base camps. Each base camp has its own log, so you can jump straight to the one you want.
The logs are written as we go, so the newest one keeps growing while we're on the road. New to the trip? Start with why we're doing it and what the Crooked Road is, then pick a base camp below.
Where it all started. We open with a Thursday night jam at the Historic Fries Theatre, spend a day in Mayberry in Mount Airy, and hear the Whitetop Mountain Band at the Rex Theater in Galax on Friday night. Along the way there's a foggy morning at camp, a visit to Creek Bottom Brewing, Dori Freeman back at the Rex, and a last campfire. Expect lots of music, small-town Main Streets, a little local history and plenty of photos.
Read Base Camp 1
We moved on to our second base camp, a three-hour, 144-mile drive, and we've been exploring since. So far: Pinnacle Overlook at Cumberland Gap with views across three states, a burst hose and a Lowe's run, the chairlift and railroad tunnel at Natural Tunnel State Park, the Wilderness Road Blockhouse, and catered barbecue and a bluegrass band at camp. This log is still being written as we go.
Read Base Camp 2We haven't gotten there yet. When we do, its log will go up here with a hero photo, a short summary and day-by-day entries, just like the first two.
Coming soon