Jacob's Ladder Trail (US-20)
A 35-mile scenic byway on U.S. Route 20 through the southern Berkshire foothills, designated by Massachusetts in 1992 and originally opened in 1910 as 'the First of the Great Mountain Crossovers.' The route winds through Lee, Becket, Chester, Huntington, and Russell, crossing the Westfield River valley with forested hills, open fields, steep rock ledges, and wetlands. It roughly parallels the Mass Pike but sees a fraction of the traffic, making it a pleasant back-road alternative with continuous rural character. Historically part of the transcontinental Yellowstone Trail.
What you'll hit along the way.
Rider-verified stops, overlooks, fuel, and the corners worth knowing about — in the order you'll meet them.
Sunco
Convenient fuel stop at the western start of the route before heading into the hills.
East Lee
Small town marking the beginning of the climb into the Berkshire highlands.
Chester
Mid-route town nestled in the Westfield River valley, good place to stretch and take in the surroundings.
Russell
Eastern end of the Jacob's Ladder corridor where the terrain opens up toward the Pioneer Valley.
No runs logged on this road yet — be the first.
Runs are rider-logged & GPS-traced in the app
Ride your own ride — times are rider-logged & GPS-traced, never a race on public roads.
Shot by the riders who've run it.
Riders upload photos to their profile and tag the road or stop — tagged shots show up here automatically.