During the first half of the twentieth century, a unique style of guitar playing known as Kentucky thumbpicking was developed by a handful of musicians in the western coal field region of Kentucky. This guitar tradition was elevated to national prominence by country guitar virtuoso Merle Travis. Subsequently, this style became characterized as "Travis Picking." Kentucky thumbpicking incorporates a steady and muted bass line that alternates between the root, fifth or third of a chord. The bass is also accentuated with the use of a thumbpick worn on the right hand. Simultaneously, the index, occasionally middle and ring fingers, play the harmony and melody on the upper strings of the guitar in a syncopated rhythm. Thumbpicking is venerated because of its reverence for individualism and adaptability. One of the primary reasons it has become so prominent is because of its flexibility; it is able to be adapted to various types of music. An historical overview of Kentucky thumbpicking is provided in order to trace its origins and development as well as explaining the style’s technical traits. Arrangements of a select few songs from the advent of this style’s development are transcribed and discussed in order to demonstrate how this repertoire translates to the classical guitar and guitar playing techniques. Insight from the perspective of a classically trained guitarist will illustrate how thumbpicking procedures can be incorporated into the classical guitar repertoire. Thereby introducing Kentucky thumbpicking to a new audience.