SR 299 begins at an intersection with US 11/SR 58 northeast of Wildwood.

The highway heads west for one mile toward an interchange with I-24/SR 409 (Exit 169) before traveling through the unincorporated community of Hooker.

The highway continues west toward the Tennessee state line where the road continues as Tennessee State Route 134.

Unlike most west-to-east routes in the United States, SR 299's mile markers increase while traveling westbound rather than eastbound.

The entire route is in Dade County.