From its western terminus, KY 44 heads eastward for 0.558 miles (0.898 km) passing a mobile home park and crossing over Pond Creek in some woods before entering into Bullitt County.

Once in Bullitt County, KY 44 becomes Shepherdsville Road and passes a couple of houses and a mobile home park before crossing over a railroad.

The route continues to head eastward through a wooded area, notably intersecting the access road to Knob Creek Gun Range (Ritchey Lane), before entering a more open area with more houses lining the road roughly 1.5 miles (2.4 km) from the Jefferson County line.

Roughly 10 miles (16 km) from the Jefferson County line, KY 44 enters the city of Shepherdsville, where it becomes West Fourth Street.

Washington Road as it continues eastward out of Shepherdsville and passes through a residential area with many homes and subdivisions lining the route.

It then passes Spencer County High School and meets the western end of the KY 55 overlap where it turns east out of Taylorsville and becomes a 4-lane divided highway known as Little Mount Road.

In Shelby County, the road becomes Southville Pike and curves northeast passing by occasional houses and open fields.

Roughly 4.5 miles (7.2 km) from Southville, KY 44 enters Mount Eden and travels along the Shelby-Spencer County line for a short distance.

KY 44 finally crosses back over into Spencer County 2.7 miles (4.3 km) southeast of Mount Eden.