 VT 153 is entirely town-maintained and goes through Bennington and Rutland counties.VT 153 begins at the state line adjacent to Washington County, New York, where it connects to County Route 153 (CR 153, formerly New York State Route 153 or NY 153) in the Rupert Valley.The route heads to the northeast, passing through the village of West Rupert, which is located northeast of the Big Ridge, a mountain.