Every route here got driven before it got offered, some of them more than once, until the wrong turns were gone and the rest were in the right order.
They stay small on purpose. A route that flows with a dozen cars comes apart with thirty. When one's ready, it goes on the list. Until then, it waits.
Out of Thomaston, CT early. Group lunch in Great Barrington, MA. Then the long way back. A hundred miles, give or take, with select regroup moments along the drive.
June 7 · CT · MAThree states and over 150 miles in a day, and you barely notice the borders. Connecticut hills give way to the quiet roads over the New York line, then back through the southern Berkshires.
July 12 · CT · NY · MAEast along the coast into Rhode Island. Less climbing, more rhythm and pace.
August 30 · CT · RIThe one that needs more than a day. Up into the Adirondacks for a weekend: real roads, a place to stay, and time to slow down between them.
Accommodation details on request.
September 26–28 · NYBack to the northwest corner for the color. Low, twisting roads through the hills and the hollows between them.
October 18 · CTThe last one before winter closes in. West over the Hudson and towards the Catskills. Weather permitting.
November · CT · NYIf it feels right,
you'll know where to look.