Route 6 West approaching the Bear Mountain Bridge has to be the most twisty, serpentine windy road I've ever been on, and to top it off, it is on the edge of a mountain cliff overlooking the Hudson River. Locals have dubbed it the "Goat Trail."
The Goat Trail starts northwest of Peekskill, NY and culminates at the Bear Mountain Bridge, which joins the far northwest corner of Westchester to southeast Orange County. The mountain it is carved into has been known since colonial times as "Anthony's Nose." The road itself is over 400 feet above the river.
How twisty is this road? Click on the video. This is not for people with vertigo.