Taconic Trail · Petersburg Pass

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.

The Taconic Trail is a state scenic byway, and the section from Williamstown to Petersburg Pass crosses the Taconic Range right at the New York line. At the pass, the Taconic Crest Trail crosses the road, and the overlook looks back over Williamstown and toward Mt Greylock. Williamstown itself is home to Williams College and the Clark Art Institute.

The New York side is farm country: NY-22 follows the narrow valley of the Little Hoosick through Petersburgh and Berlin, between two wooded ridges, and continues south to Stephentown; Petersburgh itself was formed in 1791, partly from land of Stephentown. The return on NY-43 and MA-43 crosses back into Massachusetts through Hancock, past Jiminy Peak, and follows the Green River north to Williamstown. Fuel in Williamstown, since there are few stations on the loop.