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Climbing Jacob’s Ladder into the Berkshires

A salute to one of the pioneering American road trips

The rocky face of the Russell Mountain Formation pokes out over the Westfield River at the eastern end of the Jacob's Ladder Scenic Byway.David Lyon

Next time you’re headed to the Berkshires, take the road less traveled for a journey into the early days of auto touring. Specifically, get off the Mass Pike at exit 3 in Westfield to drive 35 miles of Route 20 over the Berkshire Hills along the Jacob’s Ladder Scenic Byway. Back in 1910, roughly 4,000 people gathered at the 1,775-foot summit of Morey Hill in Becket for the official opening of the first over-mountain highway built specifically for the new-fangled horseless carriages. Within a decade, driving enthusiasts around the region were testing the mettle of their machines on this high road.

With its twists and turns, climbs and dips, and occasional scenic vistas, the Jacob’s Ladder Scenic Byway is fun to drive in a single nonstop swoop. But it’s even better if you take it slow to savor some of the villages, historic roadside rest stops, and state forest land. There are plenty of hiking trails to stretch your legs.


The trail begins officially at the Westfield-Russell town line where you’ll see the first of the Jacob’s Ladder Scenic Byway signs that mark the route. The really curious should be prepared to pull over frequently to read the information panels posted at roadside turnouts. The first, in Russell, hints of a lost world of bustling industry in the southern Berkshires. Russell’s three paper mills, for example, produced glassine, artificial leather for shoe soles, and Strathmore fine writing and artists' papers. Most of the little villages with their high-spired white churches are just a quick right turn from the byway.

This double keystone arch railroad bridge, constructed 1839-41, still carries freight trains over the west branch of the Westfield River. It's located near the trailhead of the Keystone Arch Bridges Trail. David Lyon

You’ll catch tantalizing glimpses of the Westfield River as you continue west. If you want to channel early auto touring pioneers, stop for a picnic at the roadside pullout in Huntington. By 1929, it had become a favorite spot for folks on newly popular ‶Sunday drives.″ It sits at the most challenging set of rapids on the Westfield River and the site of an annual whitewater canoe race downstream to Russell. This has been such a dry year that the federally designated ‶Wild and Scenic River″ is but a lazy trickle over the rocky river bed.


Three and a half miles farther along the scenic byway, watch for a parking area on the left for Boulder Park ( This corner of the Chester-Blandford State Forest was developed as a day-use recreation site by the Civilian Conservation Corps in the 1930s. Following the Park Rustic style created by Daniel Ray Hull for the National Park Service, the CCC workers incorporated local logs and stones to build a number of structures, including a picnic pavilion, wooden bridges, and a now-drained swimming hole. You might feel like the 12-year-old protagonists of ‶Moonrise Kingdom″ as you ascend the hillside’s stone steps or ramp overgrown with spongy sphagnum moss to walk along the flat, wide trail through the woods.

Another five miles west, Carm’s Restaurant & Coffee Shop occupies a former gas station, complete with a classic Pegasus Mobil sign at the crest of the facade. At the next major right off Route 20, follow the left fork for Middlefield Road. In 2.6 miles, you’ll see trailhead parking for the Keystone Arch Bridges Trail on the left. The first stone railroad bridges in the country are a source of considerable local pride. The keystone arch structures were built 1839-1841 of cut stones fitted together without benefit of mortar or steel reinforcements. A few washed out in a 1927 flood, but the trail leads to views of several remaining bridges.


Most walkers access the Boulder Park walking trail by climbing stone steps set into the hillside by the Civilian Conservation Corps in the 1930s. David Lyon

You’ll enjoy almost instant gratification when you follow a narrow woodland path at the back of the lower parking lot. In less than 50 yards, it delivers you to a view of the only remaining double arch keystone bridge of the group. Squat and powerful as a sumo wrestler, the double-barreled bridge exudes a quiet monumentality. It was clearly built for the ages and still carries CSX freight trains nearly 180 years after it was constructed. If you want to see more bridges along the 2.5-mile wooded Keystone Arch Bridges Trail (, watch carefully for the small KAB signs marking the correct route. Since there is no outlet from the trail, you’ll have to retrace your steps.

Once you return to Route 20, the Jacob’s Ladder Scenic Byway becomes a quintessential snaking mountain road as it begins the serious ascent of the mountain range separating the Connecticut and Housatonic river valleys. A few ear-pops later (6.4 miles, to be precise), look for the big pile of stones on the right-hand side of the road. The cairn was created at the 1910 road opening ceremony as attendees brought stones from their hometowns. The heap has been moved twice, and attempts to hold it together with mortar and cement have been only marginally successful. Still, it’s nice to revisit the site of a signal event in the annals of tourism.


Visitors are free to explore the grounds of Jacob's Pillow. David Lyon

The scenic byway is literally all downhill from here. Just 1.8 miles past the cairn, George Carter Road turns off to the right for a half-mile detour to Jacob’s Pillow ( The dance festival was all virtual this year and even in a normal year, performances would be over by now. But you’re welcome to walk the grounds and explore the surrounding trails. Active since 1933, it’s the Mecca of modern dance. Use your cellphone to download a self-guided walking tour by using the QR code displayed on information panels.

The descent along Route 20 to Lee has the same snaking quality as the ascent from Chester, but it’s even more fun when you’re driving downhill. Lee actually feels like a big city after the untrammeled wilds of the hill-town villages. It’s nice to see that Joe’s Diner, site of a famous Norman Rockwell image of a police officer and a young boy on adjacent stools, is open again — with social distancing of course. (No recreating the scene.) The official end of the byway comes up at lovely Laurel Lake on the Lee-Lenox town line. Like the auto pioneers of old, you have arrived in the Berkshires.

Contact Patricia Harris and David Lyon at

For more information on the Jacob’s Ladder Scenic Byway, see

Designated a ‶Wild and Scenic River,″ the Westfield is a dry and shallow shadow of itself in this drought year. It parallels the scenic byway from Westfield to Becket. David Lyon

Patricia Harris can be reached at David Lyon can be reached at