- Western Terminus:
- Main Street (US 44/NY 55) in New Paltz
- Eastern Terminus:
- US 9W in Highland
- 12.55 miles
NY 299 is an east/west route in Ulster County. It begins at US 44/NY 55 just east of the Shawangunk Ridge and runs east to New Paltz, where it is known as Main Street and is multiplexed with NY 32 for a few blocks. After the two routes split, there is an interchange with the New York Thruway (I-87) at exit 18. NY 299 continues east to Highland, where it ends at US 9W, about a mile north of where it meets US 44/NY 55.