New York State Route 299 (NY 299) is a short but important state route entirely within Ulster County, New York, in the United States. 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. Only the eastern section is a state highway; from Shawangunk to New Paltz, it is owned and maintained by Ulster County. Route description NY 299 begins at an intersection with the concurrent US 44 and NY 55 just south of Lake Minnewaska in the town of Gardiner. NY 299 winds northeast through the deep woods of Gardiner, paralleling US 44 and NY 55 as it climbs through the Shawangunk Mountains . Passing well to the south of the hairpin turn on US 44 and NY 55, NY 299 bends eastward under control of Ulster County, with the County Route 8 (CR 8) designation. Near Hasbrouck Road, the dense woods recede and NY 299 crosses east through fields through Gardiner. Soon crossing into the town of New Paltz, NY 299 runs along the flood plain of the Wallkill River. 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. At the junction with CR 7 (Libertyville Road), CR 8 ends and NY 299 and CR 7 continue east until crossing the river into the village of New Paltz. In the village, NY 299 proceeds northeast as Main Street, reaching a junction with NY 32 (North Chestnut Street) and the northern terminus of NY 208 (South Chestnut Street). NY 299 and NY 32 become concurrent through the village, crossing through the commercial center of the village on Main Street. The routes bend eastward at North Front Street, crossing through a residential/commercial section of the village. At the junction with Manheim Boulevard, NY 32 turns off to the south while NY 299 continues eastward along Main Street. After leaving downtown New Paltz, the route re-enters the town of New Paltz, crossing into exit 18 of the New York State Thruway (I-87). Continuing east along Main Street, NY 299 continues through the town of New Paltz, crossing the northern terminus of CR 22A (South Ohioville Road). Paralleling a former alignment of itself, NY 299 crosses through the hamlet of