Kentucky Route 299 (KY 299) is a 12.3-mile-long (19.8 km) state highway in the U.S. state of Kentucky. The highway connects mostly rural areas of Calloway and Marshall counties.

KY 299 begins at an intersection with KY 94 northwest of Wiswell, within Calloway County. It travels to the north and crosses over the West Fork Clarks River. 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 West Fork Rockhouse Creek. It enters Kirksey, where it intersects KY 464 (Backusburg Road/Kirksey–Almo Road). After it crosses over the North Fork Duncan Creek, it enters Marshall County and meets its northern terminus, an intersection with KY 402 (Brewers Highway).

County	Location	mi	km	Destinations	Notes
Calloway	​	0.0	0.0	KY 94	Southern terminus
	​	3.1	5.0	KY 121 west	Southern end of KY 121 concurrency
	Stella	3.6	5.8	KY 121 east	Northern end of KY 121 concurrency
	​	4.5	7.2	KY 80 – Mayfield, Murray
	Kirksey	7.7	12.4	KY 464 (Backusburg Road/Kirksey–Almo Road)
Marshall	​	12.3	19.8	KY 402 (Brewers Highway)	Northern terminus
1.000 mi = 1.609 km; 1.000 km = 0.621 mi       Concurrency terminus

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