The highway connects Southern Vermont's primary towns of Bennington and Brattleboro via its crossing of the Green Mountains.

A short distance west of the state line, NY 7 has a junction with the west end of the Bennington Bypass (VT 279 in Vermont), a two-lane freeway that allows VT 9 traffic to bypass the center of town.

VT 9 heads east as West Road and passes south of William H. Morse State Airport and has a pair of sharp curves as it passes through Old Bennington, which is south of the Bennington Battle Monument and north of Southern Vermont College.

VT 9 reaches the source of City Stream at Big Pond and summits the Green Mountains.

VT 9 enters Windham County and the town of Wilmington just west of the Harriman Reservoir.

The route passes Molly Stark State Park and enters the town of Marlboro west of the summit.

VT 9 passes to the north of the center of Marlboro and enters the valley of Whetstone Brook, which the highway follows into the town of Brattleboro.