Karen and I are proud board members of the present day Jacob’s Ladder Trail Scenic Byway aka Route 20. History is here in the Hilltowns! The JLT includes Russell, Huntington, Chester, Becket and Lee. Here’s some background courtesy of Becket Historical and a great website by Bruso. https://homepages.rootsweb.com/~shirleyb/jacobsladder/grow.html

What we know of today as the Jacob’s Ladder Trail (Route 20) began as a series of connected local roads in the early nineteenth century which eventually became part of the “Becket Turnpike”, a proposed route between Springfield and the Berkshires. But in its early days it was known to the earliest automobile drivers as a treacherous route with steep grades, frequent washouts and disabling mud.

Locals referred to it as the Jacob’s Ladder, said to be a reference to the appearance of the many water bars placed across the road to channel water off the road, giving the road a “ladder-like” appearance. Motorists using the route were not as kind, dubbing one of the steepest hills the “three-dollar hill” as that was the usual rate charged by local farmers to pull their automobiles out of the mud with their oxen teams.

In 1904 “The Horseless Age”, a magazine devoted to the new marvel of automobile travel, reported that the Automobile Club of America was proposing “to post signs in Blandford and Becket warning automobilists against taking the Jacob’s Ladder route from Springfield to the Berkshires.”

Deemed safer by the Automobile Club were routes from Chester through Middlefield, Hinsdale, Dalton and Pittsfield, or from Russell through Blandford, Otis and Lee.

In that same year Cortland F. Bishop, a wealthy resident of Lenox and an avid motorist, began his long campaign to improve Jacob’s Ladder and convinced the Becket Selectboard to allocate public funds for addressing the most hazardous portions of the road. At the same time he advocated in Boston for the state to take over the maintenance of the road. In this quest he was assisted by Senator Allen T. Treadway, who also happened to own the Red Lion Inn which would benefit from a direct and safe route into the Berkshires.

Their efforts paid off and the state began improvements to the road, culminating with the official celebration of the completion of the road in September of 1910. A crowd of around 1,000 people attended the opening ceremonies held at the summit of the road in Becket. Today there is a cairn at the site marking the summit.

The Lee newspaper, the Valley Gleaner, reported on the opening: “The breaking down the natural barrier between the east and west, the building of a highway connecting the Connecticut and Housatonic river valleys, the unifying of the state by surmounting physical obstacles, all this is meant by the completion of this project… the people of the state will henceforth know each other better because Jacob’s Ladder has been conquered.”

Just a few years later a transcontinental route across the northern United States was proposed with the new Jacob’s Ladder Trail incorporated as part of that route. It eventually became the Yellowstone Trail, spanning the country from Plymouth, Massachusetts to Seattle, Washington, thus cementing the Jacob’s Ladder Trail as the main east-west route into the Berkshires.

The heyday of the Jacob’s Ladder Trail as a commercial and tourism magnet was from that period until 1957 when the Massachusetts Turnpike was completed.

In the 1990’s the road was officially designated as a Scenic Byway and in 1992 the Jacob’s Ladder Trail Scenic Byway Advisory Board (JLTSB) was created with representatives of Russell, Huntington, Chester, Becket and Lee, along with representation from the local regional planning commissions. The JLTSB works to promote the scenic byway and protect its legacy as the original “mountain crossing”.

In the 1990’s the road was officially designated as a Scenic Byway and in 1992 the Jacob’s Ladder Trail Scenic Byway Advisory Board (JLTSB) was created with representatives of Russell, Huntington, Chester, Becket and Lee, along with representation from the local regional planning commissions. The JLTSB works to promote the scenic byway and protect its legacy as the original “mountain crossing”

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