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Drives

The 2026 season,
one route at a time.

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.

Adirondacks Weekend

Limited spots

The 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 · NY

Hills & Hollows

Spots open

Back to the northwest corner for the color. Low, twisting roads through the hills and the hollows between them.

October 18 · CT

Catskills Run

Planned

The last one before winter closes in. West over the Hudson and towards the Catskills. Weather permitting.

November · CT · NY

Shoreline Run

Already driven

East along the coast. Shorter stretches between stops, more rhythm than pace, taken slow with the water in view most of the way. The regroup points this time are a few shoreline hotels worth walking into.

August 30 · CT

Tri-State Loop

Already driven

Three 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 · MA

Berkshire Run

Already driven

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 · MA

If it feels right,
you'll know where to look.

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