Rockbridge County is quietly exceptional for cycling. You get real climbs, real valleys, and roads that still feel agricultural rather than optimized for speed. Over time, a handful of routes have become my go-tos—not because they’re the hardest or longest, but because each one has a clear personality. These are five rides I return to again and again.
Glasgow
The Glasgow ride is about flow and distance. It’s the route I reach for when I want to settle in, find a rhythm, and let the miles stack without constant interruption. The terrain rolls rather than punches, and the road pulls you through open farmland and small-town edges in a way that feels continuous. It’s mentally easy in the best sense, with enough variation to stay interesting, but predictable enough that you can think, listen, and just ride. This is my “clear the head” loop.
Big Hill
Big Hill does exactly what it promises. This is a short, honest test, with one main effort that defines the ride. I like it when I’m time constrained or when I want a reminder that strength still matters. There’s something satisfying about a route that doesn’t pretend to be subtle. You warm up, you climb, you deal with it, and then you’re done. It’s not a scenic ramble; it’s a benchmark.
Plank Road
Plank Road is another go-to. I love this one because it’s understated and local in the best way. It feels like a road that exists for the people who live there, not for people passing through. The riding is steady, the surroundings are quiet, and the experience is tactile with changes in pavement, light, and grade that reward paying attention. This is a route I ride when I want to feel in the county rather than moving across it.
Church (Parkway)
I recently had the pleasure of riding the Blue Ridge Parkway for the first time, and immediately fell in love with it. This ride has a split personality, which is exactly why I like it. You move from small roads into the Parkway, and suddenly the scale changes. The traffic disappears, the views open up, and the effort becomes long and measured. It’s not about speed; it’s about patience and cadence. The Parkway section gives the ride a sense of occasion, and the approach and return (lots of downhill!) keep it grounded.
Goshen Pass
Goshen Pass is the most “Virginia” of the five. Water, rock, trees, and a road that threads through it all. It’s a ride I save for days when I want to feel small in a good way. The pass itself demands respect, but the payoff is immersion—cool air, sound, and texture. This is less about training and more about being reminded why riding outside still matters.
None of these rides are exotic, and that’s the point. They’re repeatable, legible, and tied to place. Together, they’re my personal map of Rockbridge County—five ways of seeing the same landscape, depending on what kind of day I’m having.