America's Scenic Byways

Jacob's Ladder Trail (Route 20)

33 miles -

Jacob’s Ladder Trail Scenic Byway is an untouched rural roadway that runs through the foothills of the Berkshires in western Massachusetts. Follow the byway through vistas of forested hills, the rock-strewn Westfield River, open fields, small towns, wetlands and steep rock ledges.

While driving the byway, you’ll see towering ledges which are sometimes laced with ice or running streams. Pass through several small towns and villages where a church spire is the highest building in sight. Explore the outskirts of the towns and villages and look for scattered homes, a few barns, a motel from the 1930s, and a campground set back from the road on a pond or stream. There are three entries into the Chester-Blandford State Forest where you can find parking areas for hiking, camping, cross-country skiing, and snowshoeing.

Stop at a historic granite quarry in Becket that operated into the 1950s, where the water-filled quarry, the 19th-century equipment, and vast piles of tailings are all still in place to illustrate the industry in a natural woodland setting.

Try taking part in art performances in the natural landscapes of the byway. At Jacob’s Pillow Dance Festival in Becket a National Historic Landmark, attend performances from dance companies that come from throughout the world. The Jacob’s Pillow Dance Festival is set within the buildings of an 18th-century farmhouse and barn, and its outdoor stage has a beautiful view into the Berkshire Hills. You can also attend performances of the Chester Theatre Company and the Vincent Dowling Theater Company, which both draw actors from national and international stages to the Chester Town Hall Theater in a National Register Historic District. Drive about four-and-a-half miles off the byway and attend the Tanglewood Summer Concerts performed by the Boston Symphony Orchestra and guest musicians. Enjoy the rural Tanglewood views of the Stockbridge Bowl and the distant Berkshire Hills. Closer to the byway, you'll find the Lenox home of novelist Edith Wharton, The Mount, a museum with restored designed gardens. One mile beyond The Mount, you can attend theatrical productions of plays at Shakespeare and Company or visit the museum of the Gilded Age at the Great Estate Ventfort Hall.

If you enjoy 19th-century architecture in its original setting, spend time in Lee Center, which has been a movie set more than once. The smaller town centers of Chester, Russell and Huntington offer many resources, including a restored railroad station from the 1840s, an Italianate Grange Hall, two mill villages, and churches with spires that mark the horizon from different locations on the byway.

Whether viewing the landscape alone, walking on old trails in the woodland forests along the byway, or attending cultural events in unspoiled landscape settings and historic districts, you'll become a part of the pristine natural world that characterizes Jacob’s Ladder Trail Scenic Byway.