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The Atlas/Massachusetts/Jacob's Ladder Trail (US-20)

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.

44 mi
Length
0
Verified stops
—
High point
Scenic
Road type
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// Nearby & related
RouteMassachusetts
6.5/10
Berkshire Highlands (MA-112)
Massachusetts
Route 112 runs north-south through the central Berkshire highlands from Huntington north through Plainfield and Colrain, connecting the Jacob's Ladder corridor (US-20) to the Mohawk Trail (MA-2). The two-lane road rolls through open farmland, cuts through tunnel-like tree canopy, and passes small hilltowns with minimal traffic. Used by local riders as a north-south spine linking the two great Berkshire east-west routes into a full-day loop. The landscape is more rural and less-traveled than parallel US-7.
53
miles
StopMassachusetts
Bridge of Flowers
Massachusetts
A 400-foot pedestrian footbridge spanning the Deerfield River in the village of Shelburne Falls, converted from a 1908 trolley bridge into a continuous flower garden open April through November. The bridge holds more than 500 varieties of plants and connects Shelburne Falls to Buckland across the river. The glacial potholes — the world's largest recorded collection, some up to 39 feet in diameter — are visible from a viewing area steps away at the base of Salmon Falls. A short walk from the Route 2 corridor.
StopMassachusetts
Gloucester Fishermen's Memorial
Massachusetts
A bronze statue of a helmsman erected in 1925 on Stacy Esplanade along Gloucester's working waterfront, honoring the 5,368 Gloucester fishermen lost at sea since the city's founding in 1623. The memorial sits on South Stacy Boulevard overlooking Gloucester Harbor, steps from active fish piers, seafood restaurants, and the route around Cape Ann (MA-127/127A). It is the starting/ending landmark for the classic 54-mile Cape Ann motorcycle loop.