Kentucky Route 1958
|Maintained by KYTC|
|Length:||8.669 mi (13.951 km)|
|South end:||KY 627 in Winchester|
| US 60 in Winchester
I-64 in Winchester
|North end:||KY 2888 in Winchester|
Kentucky Route 1958 (KY 1958) is an 8.669 mile (13.951 km) long state highway in the Winchester, Kentucky area. The route, a bypass circling the perimeter of the city, is defined by the Kentucky Transportation Cabinet as a north–south route despite the east–west alignment the bypass follows for most of its length. Its southern terminus is at Kentucky Route 627 (former US 227) a quarter-mile south of Interstate 64 exit 96 north of the city. The northern terminus is at Kentucky Route 2888 (Rockwell Road) mere yards from I-64 northwest of downtown.
The 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.
From KY 627, KY 1958 heads clockwise around Winchester to Kentucky Route 89. Here, the route turns west and embarks on a pair of concurrencies with KY 89 and KY 627 through downtown to access the original bypass southwest of Winchester. Upon reaching the bypass, KY 1958 separates from KY 627 and follows the highway clockwise around the perimeter of the city to KY 2888 a short distance from the I-64 interchange.