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KY 299 begins at an intersection with KY 94 northwest of Wiswell, within Calloway County. It travels to the north and crosses over the . It continues to the north and intersects KY 121. The two highways travel concurrently to the east-southeast. In Stella, they split, with KY 299 resuming it northward trek. Southwest of the Murray-Calloway County Airport, it intersects KY 80. The highway crosses over the . It enters Kirksey, where it intersects KY 464 (Backusburg Road/Kirksey–Almo Road). After it crosses over the , it enters Marshall County and meets its northern terminus, an intersection with KY 402 (Brewers Highway).[1]