Location: Western Massachusetts
Length: 25 miles (40.23 km)
Time To Allow: 1 – 2 hours

Description/Highlights/Points of Interest

Jacob's Ladder Trail Scenic Byway originated centuries ago when people from the Mohican and Woronoake tribes walked between Connecticut and the Hudson River valleys. The trail has now been transformed into one of the most beautiful roads in the United States. During 1910, authorities had the road built as the first highway specifically constructed for the new state-of-the-art horseless wagons, or automobiles. Adventurers from many places came to test themselves and their machines against the rugged terrain. At the time, there were potholes that could hide a tire, mud so deep it could bury a car, and small boulders blocking the road. Today, however, Jacob's Ladder Trail Byway is a pleasant drive for motorists of a less venturesome sort. Many have appreciated the inspiring landscape of the Berkshire Hills while driving this relaxing route.

Not long after the road was built, it became known as the "Yellowstone Trail." This was because it joined with a highway that linked the Atlantic and Pacific oceans together. The road stretched from Boston to Oregon. However, locals know this byway best as "The First of the Great Mountain Crossovers" because of the audacity and vision the engineers demonstrated by constructing this road over the wild mountains and through Jacob's Ladder Corridor.


The following organization offers trips in Massachusetts:

Grand Autumn New England
Tauck World Discovery
Enjoy four two-night stays in the classic destinations of autumn New England! Our longest fall foliage excursion gives you more time to explore spectacular landscapes vibrant in color, steeped in historical attractions, and brimming with charming "Americana." Travel from New York City through the states of New York, Vermont, New Hampshire, Maine, Massachusetts, Rhode Island and Connecticut for the quintessential journey through autumn New England.

Classic New England
Tauck World Discovery
This classic vacation reveals a wealth of splendors! Picture New England's waking meadows sweet with fragrant air, summer sails and brisk breezes as you wander through old mansions, museums and places from history books. Rich in tradition and brimming with antique charm, there is no corner of North America as picturesque, diverse or culturally rewarding.