KY 44 originates at a junction with U.S. Route 31W and U.S. Route 60 (known as Dixie Highway) as a two-lane undivided highway northeast of West Point in far southwestern Jefferson County at the banks of the Ohio River. 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.
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. At Hilltop Road, KY 44 curves toward the south, then back toward the north, before heading east again. Roughly 10 miles (16 km) from the Jefferson County line, KY 44 enters the city of Shepherdsville, where it becomes West Fourth Street. The route intersects with KY 61(Buckman Street/Preston Highway) in Shepherdsville, a route running north into downtown Louisville. KY 44 then becomes East Fourth Street and 0.725 miles (1.167 km) from KY 61 it meets Interstate 65 at Exit 117. Interstate 65 also runs north into downtown Louisville, or south to Bowling Green and Nashville.
East of I-65, KY 44 becomes Mt. Washington Road as it continues eastward out of Shepherdsville and passes through a residential area with many homes and subdivisions lining the route. A few miles east of Shepherdsville, KY 44 enters the city of Mount Washington. In Mount Washington, KY 44 intersects with US 31E/US 150, also known as Bardstown Road. Bardstown Road runs northeast into downtown Louisville and all the way south to the Tennessee state line. The route continues to head east out of Mount Washington and into Spencer County roughly 2 miles (3.2 km) east of Mount Washington.
Spencer County
Once KY 44 enters Spencer County, it crosses over Dutchman Creek 0.418 miles (0.673 km) from the Bullitt County line. East of Dutchman Creek, the road curves southeast, passing through Waterford. From Waterford, the route continues eastward past Spencer County Middle School and Spencer County Elementary School, and enters the city of Taylorsville roughly 8.5 miles (13.7 km) from the Bullitt County line.
In Taylorsville, KY 44 becomes West Main Street until it overlaps with KY 55, where it becomes East Main Street. Less than one mile from the western end of the KY 55 overlap, KY 44 turns north out of downtown Taylorsville and crosses over Brashears Creek. 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. The highway curves northeast a few miles east of Taylorsville, passing north of Taylorsville Lake. KY 44 meets the western terminus of KY 248 around 5 miles (8.0 km) northeast of Taylorsville. It turns north toward Shelby County and narrows to two lanes. 3 miles (4.8 km) north of KY 248, KY 44 enters Shelby County.
Shelby County
In Shelby County, the road becomes Southville Pike and curves northeast passing by occasional houses and open fields. KY 44 meets the southern terminus of KY 148 1.237 miles (1.991 km) from the Spencer County line and continues for 2 miles (3.2 km) longer where it meets KY 53 and KY 714 in Southville. The route then becomes concurrent with KY 53 (Mount Eden Road) as it turns toward the southeast. 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. Roughly 1 mile (1.6 km) down the road, the route crosses over into Anderson County.
Anderson County
In Anderson County, the road travels toward the south, then curves toward the southeast, and then toward the east. 3.8 miles (6.1 km) from the Spencer County line, the route meets the eastern end of the KY 53 overlap in Glensboro, where it becomes Glensboro Road. It continues eastward, passing through Anderson City and meeting the southern terminus of KY 395 east of Anderson City. Roughly 2 miles (3.2 km) east of KY 395, the road curves toward the north, then back toward the east at McDonald Road. KY 44 enters the city of Lawrenceburg where it intersects with US 62 Truck/US 127 Bypass, also known as the Lawrenceburg Bypass or Bypass North. The route ends at its eastern terminus at an intersection with US 127 and US 62 1 mile (1.6 km) further east.
History
Sections of Route 44 in Bullitt County follows the Wilderness Road, a historic wagon road established in the early 19th century.[2]
