Kentucky Route 1958 (KY 1958) is a 5.325-mile-long (8.570 km) state highway in Clark County, Kentucky, that serves as a bypass route around Winchester.

The western segment, which is 2.953-mile-long (4.752 km), runs from Kentucky Route 627 in southwestern Winchester to Kentucky Route 2888, Revilo Road, and Rolling Hills Lane northwest of Winchester.

However, the concurrencies are unsigned and the eastern segment's signed cardinal directions are opposite of those on the official log.

The western bypass was originally a connector route between I-64, Van Meter Road, Rockwell Road and US 60, but was extended south and southeast to KY 627 south of the city and, later, to its present terminus north of Winchester.

It will be extended westward to the western bypass, making for a semi-loop around the city.