It begins at an intersection with KY 181 just north of Elkton about north of the present route of U.S. Route 68. The route passes through mainly rural areas of Todd County and has an intersection with KY 171 and after that, a crossroad intersection that marks the eastern terminus of KY 507, and the western terminus of KY 178. It then goes through the unincorporated community of Sharon Grove, where a roadside market called the "Hwy 106 Market" is located at a crossroad intersection with two local county-maintained roads, Mount Sharon Road and H Gorbel Road. After passing through Sharon Grove, the highway enters Logan County about a few feet east of the intersection with Crawford Road, and then has intersections with KY 2376, and another one with KY 1151, both are secondary routes in Logan County. The highway makes it to Lewisburg, and runs concurrently with US 431. Only a few hundred feet away from that intersection, the highway intersects KY 107. A few hundred more feet after that, KY 106 breaks away from US 431, and follows Stacker Street into downtown Lewisburg. After passing through Lewisburg, KY 106 then goes through rural areas of northern Logan County, crosses the Mud River, and then enters Butler County just south of the small town of Quality where it runs concurrently with KY 1153 for about. Despite being an even-numbered state highway, KY 106 becomes a north-south oriented roadway upon entry into Butler County. KY 106 has two more intersections KY 1187, and then KY 949 before reaching its end just north of Huntsville at an intersection with KY 70, the major artery connecting nearby Rochester to the Butler County seat, Morgantown.
History
KY 106 originally began at Allegre when it was first commissioned in 1929. At some point in the late 1940s, KY 106 was extended further northwest to Kirkmansville, west of Clifty. After that point in time, It followed the course of the current KY 171 from the KY 107 junction to where KY 171's current terminus is located. At sometime between 1969 and 1972, KY 106 was rerouted onto Blue and GrayPark Road off KY 181 just northeast of Elkton and it makes a right turn onto its current alignment, with KY 171 being extended to include its current run through Allegre, across KY 181, and ending at this intersection. The original alignment of Kentucky Route 344 followed Blue and Gray Park Road during the 1930s and 1940s. KY 344 originally served the now-defunct Blue and Gray State Park.
