US-250 · Staunton to Monterey

Two mountains back to back, one way: from Staunton the route follows US-250 west through Churchville, climbs Shenandoah Mountain past the Confederate Breastworks, drops to McDowell and climbs again over Bullpasture Mountain before finishing in Monterey. It's 43 miles. There are few services along the way, so fuel up in Staunton, and expect patched pavement in places and cattle in the valleys. The route ends in Monterey on purpose: farther west, US-250 climbs into West Virginia.

US-250 leaves Staunton to the west and crosses farm country through Churchville before the first climb, Shenandoah Mountain. At the top, on the line between Augusta and Highland counties, is Fort Edward Johnson, the Confederate Breastworks: trenches dug in April 1862 that are still visible, with a Forest Service parking lot, an interpretive half-mile loop and wide views west over Highland County. The road then drops to McDowell, the village where the Battle of McDowell was fought in 1862.

After McDowell the road climbs again over Bullpasture Mountain and comes down to Monterey, the county seat of Highland County, one of the least populated counties in Virginia. High's Restaurant on Main Street has been there for decades. In March the Highland Maple Festival fills the town (in 2026 it ran on March 14-15 and 21-22). Services are few along the whole route, so fuel up in Staunton, and expect patched pavement and cattle near the road. It's a one-way route and it ends in Monterey on purpose: west of town US-250 climbs Allegheny Mountain into West Virginia.