It extends for 13.14 miles (21.15 km) from the New York state line at Rupert to VT 30 in Pawlet.

Route 153 then heads northward, intersecting local roads and parallelling the state border.

Highgo Hill is passed to the west, and is only accessible via Chef Clark Road.

[4] Route 153 then edges closer to the state border, entering West Pawlet.

The river parallels Route 153 for the rest of its length until its terminus at VT 30 in Pawlet.