 Jacob's Ladder Trail traverses the scenic southern Berkshires. The scenic byway follows the same rivers and streams that guided native Americans of the Mohican and Woronoake tribes as they traveled between the Connecticut and Hudson River valleys. In 1910, the road was opened as the first highway built specifically for the revolutionary new horseless carriages. Crossing the Berkshires as it does, it was dubbed "the First of the Great Mountain Crossovers,". The Trail attracted automotive pioneers from far and wide to test themselves and their machines against the rugged terrain. Within a few years, the Trail had become a part of a continent-spanning highway linking Boston and Oregon, known as the "Yellowstone Trail."
 The Trail has evolved in the nearly 100 years since its opening. It gained in popularity with motoring tourists through the decade of the 1920s. With the great depression and World War II, tourism declined. Jacob's Ladder Trail became a major trucking route in the middle part of the century, offering, as it did, an efficient route from Boston and Springfield to Albany and points west. With the inauguration of the interstate highway administration in the Eisenhower administration, plans were developed to build the Massachusetts Turnpike. With the opening of that road, with its higher speeds, multiple lanes and easier grades and turns, Jacob's Ladder Trail became a backwater virtually overnight.
 The siphoning of traffic from Jacob's Ladder Trail by the Mass Pike has had a range of effects on the towns along the trail - some good and some not. Gone is the steady flow of truck traffic through the little towns and hamlets, but also gone is much of the economic vitality of the region. The paper, textile and other manufacturing mills that once dotted the Trail are mostly gone. Modern tourists benefit from the shift brought about by the turnpike. The region has been spared much of the development that has transformed other parts of New England, preserving a slice of history.
The 33-mile segment of Route 20 from the Lee town common in the west to the Russell/Westfield town line in the east was designated as a state scenic byway by an act of the legislature in 1992 - only the second road in the state (after Route 6A on Cape Cod) to be recognized as such. The designation was extended to the Lee/Lenox town line about ten years later, making the total length of the byway thirty-five miles. A coalition of citizens and professional planners, with support from MassHighway, has worked since the inception of the modern scenic byway designation, to protect the character of the road and its surroundings and to initiate and oversee enhancements.
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History of the Jacob's Ladder name
 The origin of the name "Jacob's Ladder Trail" is steeped in legend. One legend has it that it was named after the biblical Jacob, while others attribute the name to Jacob Carter, a member of the family that owned the farm on George Carter Road in Becket that is now Jacob's Pillow. The Carter family farm was near the main stagecoach route, the historic Jacob's Ladder Trail. The biblical Jacob slept on a stone pillow and dreamt of a ladder to heaven. When the Carters found a large pillow-shaped rock on their property, they named their farm "Jacob's Pillow," a name that stuck with the property and may have contributed to the name of the highway.
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The railroad and Jacob's Ladder Scenic Byway
 The railroad has played an important role along Jacob's Ladder Trail since its arrival around 1840. It brought industry and prosperity to the region, leaving a legacy that includes a series of hand-crafted keystone arch bridges of awe-inspiring proportions. Trains continue to use the tracks along the Trail to carry freight and passengers, attracting railroad buffs to photograph or simply see them against the backdrop of the Berkshire hills.
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The people of the Jacob's Ladder Scenic Byway region
 The rugged terrain of the region has always nurtured Yankee individualism. A wealth of artists and artisans have set up shop in the hills surrounding the Trail. These range from stonecutters and potters to dancers and playwrights; from crafters of wood products to crafters of words. The stoic heritage of the region is embodied by a small, but vital population of farmers raising an array of crops and animals, including blueberries and maple products, cattle, sheep and horses. Traditional natural-resource industries, such as forestry and quarrying also play a large role in the economy of the Jacob's Ladder Scenic Byway region.
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History of the Byway
Another legend recalls the similarity of the original Jacob's Ladder Trail to a ladder, interspersed as it was with waterbars or "thank-you-ma'ams" to prevent wash-outs. An embellishment on that legend has an enterprising local farmer named Jacob (perhaps the Jacob of the Carter Farm) who would flood the waterbars to create mudholes that first carriages, then automobiles would get stuck in. Farmer Jacob would then hire himself and his team of oxen to the luckless driver to tow the stranded vehicle out of the mire.
