At FFH–299, VT 155 turns northeast and crosses into Rutland County.

Now in the town of Mount Holly, the route continues along the forest border, turning northwest as Weston Road.

[3] VT 155 winds along the border northwestward for several miles, paralleling the nearby Mill River.

Bypassing the hamlet of Belmont, the route runs up the forest line, turning more towards the north.

Before the junction with Fowler Brook Road, VT 155 turns northwest again, crossing railroad tracks and into the town of Wallingford.