From Stamford · Jacob's Ladder Trail · US-20

Full-day version that starts in Stamford: it adds the ride there and back to Jacob's Ladder Trail · US-20. Here is what you'll find on the core stretch:

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.