VT 133 soon begins to wind northeast through Pawlet, soon crossing into the town of Tinmouth, bending north and bypassing the hamlet of East Wells.

Running along the side of a ridge, VT 133 becomes West Tinmouth Road, soon reaching Middletown Springs.

[4] VT 133 becomes known as South Street as it enters Middletown Springs, winding through fields and nearby golf courses, making a short northwestern turn near Daisy Hollow Road.

Crossing the Poultney River, the route enters downtown Middletown Springs, reaching a junction with VT 140 (West Street).

Through Ira, the route does sporadically cross through dense woods, turning northeast through the fields in town.