[3] Pleasant Brook is a small hamlet, consisting of a junction with CR 50 (Winne Hollow Road).

After South Valley, NY 165 continues eastward through the woods along Pleasant Brook, which soon opens into Plank Pond.

The route becomes surrounded by dense wilderness, soon making a gradual bend along the hillside down into the hamlet of Weber Corners.

Now in the town of Seward, NY 165 crosses past several residences in Weber Corners before returning to the woods to the east.

This reverts near Cemetery Road, where the route continues east past several farms and into the hamlet of Dorloo.

In the center of Dorloo, the route intersects with the northern terminus of CR 33 (West Richmondville Road).