Map of Ulster County in eastern New York with NY 299 highlighted in red | ||||
| Route information | ||||
| Maintained byNYSDOT,Ulster County and the village ofNew Paltz | ||||
| Length | 12.39 mi[1] (19.94 km) | |||
| Existed | 1930[2]–present | |||
| Major junctions | ||||
| West end | ||||
| Major intersections | ||||
| East end | ||||
| Location | ||||
| Country | United States | |||
| State | New York | |||
| Counties | Ulster | |||
| Highway system | ||||
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New York State Route 299 (NY 299) is a short but important state route entirely withinUlster County,New York, in theUnited States. Centered on its interchange with theNew York State Thruway outsideNew Paltz, it provides access from that road to the popular recreational attractions of theShawangunk Ridge to the west andPoughkeepsie to the east. Only the eastern section is astate highway; from Shawangunk to New Paltz, it is owned and maintained by Ulster County.

NY 299 begins at an intersection withUS 44/NY 55 just south ofLake Minnewaska in the town ofGardiner. 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 ofUlster 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 ofNew Paltz, NY 299 runs along the flood plain of theWallkill River.[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. At the junction withCR 7 (Libertyville Road), CR 8 ends and NY 299 and CR 7 continue east until crossing the river into the village ofNew Paltz. In the village, NY 299 proceeds northeast as Main Street, reaching a junction withNY 32 (North Chestnut Street) and the northern terminus ofNY 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.[3] 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 theNew York State Thruway (I-87). Continuing east along Main Street, NY 299 continues through the town of New Paltz, crossing the northern terminus ofCR 22A (South Ohioville Road). Paralleling a former alignment of itself, NY 299 crosses through the hamlet of Ohioville and enters the town ofLloyd. In Lloyd, NY 299 remains a two-lane commercial road, crossing a junction withCR 22 (South Street / South Elting Corners 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 amobile home park. Crossing a junction withCR 12 (New Paltz Road), the route bends northward and begins a parallel withCR 15 (South Riverside Road). CR 15 soon merges into NY 299, which continues east past a junction with another piece of CR 15 (North Riverside Road). Paralleling each other once again, NY 299 turns southeastward, continuing past residences in the town of Lloyd before reaching a junction withUS 9W. This junction marks the eastern terminus of NY 299, just north barely within town ofHighland.[3]
NY 299 was assigned as part of the1930 renumbering of state highways in New York to the portion of its modern alignment east ofNew Paltz.[2] It was extended westward to its current western terminus inGardiner in the early 1950s.[4][5]
The entire route is inUlster County.
| Location | mi[1] | km | Destinations | Notes | |
|---|---|---|---|---|---|
| Gardiner | 0.00 | 0.00 | Western terminus | ||
| Town of New Paltz | 4.87 | 7.84 | Western end of CR 7 concurrency | ||
| 5.65 | 9.09 | Eastern end of CR 7 concurrency | |||
| Village of New Paltz | 5.97 | 9.61 | Western end of NY 32 concurrency; northern terminus of NY 208 | ||
| 6.48 | 10.43 | Eastern end of NY 32 concurrency | |||
| Town of New Paltz | 7.23 | 11.64 | Exit 18 on I-87 / Thruway | ||
| Lloyd | 9.60 | 15.45 | Western terminus of CR 12 | ||
| 12.39 | 19.94 | Eastern terminus; hamlet ofHighland | |||
1.000 mi = 1.609 km; 1.000 km = 0.621 mi
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