Jacob's Ladder Trail Scenic BywayLooking to soak up some of that beautiful Berkshires scenery? Take a cruise along the Jacob’s Ladder Trail. The historic, 35 mile Scenic Byway treats its travelers to gorgeous views of the southern Berkshires between Lee and Russell, MA.

Jacob’s Ladder Scenic Byway, part of U.S. Highway 20, runs from Russell, MA, to the Lee/Lenox town line, here in Berkshire County. In between, the road takes you through the towns of Huntington, Chester, and Becket. The area has seen less development than other parts of New England, leaving it rich in culture yet charming and unpretentious.

The Trail will also take you through plenty of lush nature scenery, too. It crosses over the Appalachian Trail, through three State Forests, past Jacob’s Pillow, across Westfield River, and up Mount Tekoa. You’ll see ponds, streams, hiking trails, campgrounds, scenic overlooks, and much more.

A Little History

Jacob’s Ladder Trail Scenic Byway opened in 1910, following a native American trail that connected the Connecticut and Hudson River valleys. Called the “First of the Great Mountain Crossovers,” it was the first highway in America built specifically for automobiles.

Prior to the advent of the interstate highway system, the byway was a popular, heavily trafficked thoroughfare. During the 1920’s, it served the first waves of motor-tourism, linking Plymouth, MA with Seattle, WA as part of the continent-spanning, “Yellowstone Trail” highway. During the Great Depression and WWII, the Trail served as a major trucking route.

With the opening of the Massachusetts Turnpike in 1957, however, traffic largely disappeared from the Jacob’s Ladder Trail. Now, the well-preserved rural roadway is mostly silent, running through forested hills, open fields, quiet wetlands, and friendly small towns.

Highlights Along Jacob’s Ladder Trail Scenic Byway

Jacob's Ladder Trail Scenic Byway MapThere’s a ton to see and do along the Byway but here are a few highlights.

Appalachian National Scenic Trail
The 2,184-mile-long Appalachian Trail intersects the Jacob’s Ladder Trail Scenic Byway between Lee and Becket, MA.

October Mountain State Forest
The October Mountain State Forest in Lee is the largest state forest in Massachusetts, with 16,500 acres of wild terrain for camping, hiking, mountain biking, snowshoeing, hunting, and off-roading.

Jacob’s Pillow Dance Festival
This 150-acre Jacob’s Pillow facility is open to the public from June through August for America’s longest-running dance festival. Outdoor performances, indoor theater performances, lectures, and more.

Morey Hill Summit and Stone Cairn
A stone cairn at the summit of Morey Hill in Becket, MA celebrates the completion of Jacob’s Ladder Trail, the country’s first auto road over a mountain range. The historic landmark was built by the crowd of 4,000, who gathered to celebrate the occasion in 1910.

Chester-Blandford State Forest
The 2,308 acre State Forest contains two of the region’s most scenic waterfalls, Sanderson Brook and Goldmine Brook. Trails in the forest take you to spectacular high summit views and scenic glacial rock drifts. Learn more.

Best of all, Jacob’s Ladder Trail starts off right here in Lee, just minutes from the door of our Berkshires bed and breakfast, Applegate Inn.