Centered on its interchange with the New York State Thruway outside New Paltz, it provides access from that road to the popular recreational attractions of the Shawangunk Ridge to the west and Poughkeepsie to the east.

[3] NY 299 and CR 8 make a dart to the northeast near a dirt extension of Jacobs Lane, straightening east again at Mohonk Private Road.

[3] Bypassing the hamlet of Elting Corners to the south, NY 299 becomes a residential road through the town of Lloyd, passing north of a mobile home park.

Paralleling each other once again, NY 299 turns southeastward, continuing past residences in the town of Lloyd before reaching a junction with US 9W.

[3] NY 299 was assigned as part of the 1930 renumbering of state highways in New York to the portion of its modern alignment east of New Paltz.