Great place to start, we just take all trails back to Manhattan. And even when I got off the trail I was quickly on another greenway

And you can go the other day to connect with the rail trail that connects to New Paltz and Kingston!

Yeah I have an old favorite route that’s kinda like that

Damn that's some crazy elevation gain...but isn't a lot of that route over major roads?

Well. Yeah. No rail trail for the Cragsmoor climb. I could make reasonable cases for MOST of the “major roads” on this route, they’re not really nasty - wide shoulders and/or low car traffic. Not all. Most. But it’s a beauty of a route overall. The view at the top of NY-52 is amazing.