From Stamford · Taconic Trail · Petersburg Pass

Full-day version that starts in Stamford: it adds the ride there and back to Taconic Trail · Petersburg Pass. Here is what you'll find on the core stretch:

A loop over the Taconic ridge: from Williamstown you climb MA-2 to Petersburg Pass on the New York line, drop to Petersburgh, head south on NY-22 through Berlin and Stephentown and return to Massachusetts on NY-43 / MA-43 through Hancock. It's 45 miles: the climb is short, steep and has a hairpin, and the rest is quiet valley roads. Fuel in Williamstown. The descent on the New York side is steep, and NY-43 has poorly marked country curves.