Jacob's Ladder Trail · US-20

The classic Berkshires crossing: US-20 leaves Russell, follows the Westfield River through Huntington and Chester, climbs to the Jacob's Ladder summit in Becket and drops past Jacob's Pillow into Lee. It's 28 miles of linked bends on the climb and easier stretches along the river, good for a mixed pack. Fuel in Lee or Westfield before you start, because there's little in between. Watch the low speed limits in Huntington and Chester, and the outlet traffic as you reach Lee.

Jacob's Ladder is one of the oldest motor roads in the region: when it opened in 1910 it was the first road built for cars to cross a range of the Berkshires, and a stone cairn still marks the summit in Becket. About 4,000 people gathered there for the opening, and the cairn was piled from stones they brought from their hometowns. Below it, US-20 runs with the Westfield River and the railroad through Huntington and Chester, and the Keystone Arch Bridges, dry-laid stone railroad arches built without mortar around 1840, sit in the woods just off the route near Chester.

On the way down to Lee you pass Jacob's Pillow, the dance festival that fills Becket every summer. Most packs reach the start from the Mass Pike at Westfield and leave it again at Lee, so plan for tolls on I-90. Chester-Blandford State Forest is a good stretch-the-legs stop, and in early to mid October the whole river valley turns color, along with the traffic.