 After CR 43, NY 166 begins winding northward through Middlefield, passing a large pond on the east side of the highway.The route soon intersects with CR 52, where it bends to the northeast once again, passing Forest of Dozen Dads County Park before entering the hamlet of Five Points.Five Points consists of a few farms, but NY 166 continues northeastward out of the hamlet through Middlefield, passing several farms and residences.