It crosses into the state in the Lake Cumberland area, passing near or through many small towns, including Somerset, Stanford, and Nicholasville.

US 27 crosses into Kentucky entering the Daniel Boone National Forest in the Strunk community, just south of Pine Knot.

It veers northeast to Lancaster then northwest to the site of Camp Dick Robinson at Kentucky Route 34, becoming four lanes.

Once in Fayette County, US 27 turns into a six-lane highway passing many shopping destinations in Lexington.

At UK's Albert B. Chandler Hospital, it turns west on four-lane Virginia Avenue, then joins US 68 (Broadway) for its northeasterly journey through Lexington's central business district and the horse-farm country of Fayette and Bourbon counties.