The Trail is a 33-mile stretch of Route 20, between Russell and Lee, Massachusetts. We encourage you to drive more of the trail when you have time. Why is this road called Jacob’s Ladder? There are conflicting stories behind the name. One version attributes the name to a man, either by the name of Jacob or who looked like the Prophet Jacob. He would use his team of oxen to pull the automobiles of city folks up the steep grades of the highway. Early automobiles of the 20th century had a hard time making it to the top of the long, steep highway. In fact, in Becket, the hill is so steep it was referred to as a ladder. The other version of the story, is taken from the Old Testament story of Jacob. Jacob dreamed of a ladder placed here on earth, which reached all the way to heaven, with angels climbing up and down. “Jacob’s Ladder” served as a gateway to Heaven. Many local people find this nickname very fitting.

The road has a long and rich history, parts of the route were Native American trails running along the Westfield River, and during the Colonial Period, more trails were added for the Westfield River Highway. In the early years of the automobile, major improvements were made to Jacob’s Ladder Trail, and it was known as the first of the great state mountain crossovers and a state scenic automobile highway.

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Jacob's Ladder Business Association


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