Rail Trail

"It’s do-able as a C route, as long as the write-up is clear about the degree of difficulty.  It’s a bit more vertical than would normally be in a C route,  The leaders would also have to be very precise about pacing – doing a true 14 on flat terrain but not letting people blow themselves out early on the climb – it’s essentially a 14 mile climb with very little let-up.  C riders would need low gears to do th

This is a beautiful loop made possible by the opening of the Cuomo Bridge bike path, and for those who like mixing it up and riding both roads and rail trails.

The loop takes 9W north to Nyack, then crosses the Mario Cuomo Bridge bike path to Tarrytown, ascends up to the Tarrytown Lakes Park, then returns south on the N/S County Rail Trail  to Van Cortlandt Park continuing to the Hudson Bridge crossing and the Greenway bike path south to wherever you want to finish.

Ride starts at the northern terminus of #1 subway in the Bronx and ends with a Metro North ride home from Croton Harmon. This is a lovely, almost traffic-free ride through Westchester County (and probably the flattest route you can find there). After following the Trailways north, it encompasses three different crossings of the Croton Reservoir system. There are some unpaved sections around the reservoir area, but they are doable on a road bike. Before getting on the train home, stop at the Blue Pig for ice cream. 

If you want to start doing self-contained touring but want to start small, here's the perfect bike overnight. Day 1 is quite easy, using the South & North County and Putnam Trailways to just above Brewster (Sears Corner). It's 55 miles and 2200 vertical feet. Day 2 is more challenging (but shorter - about 42 miles and 2900 vertical feet) with more climbing and several steeper sections, but it goes past beautiful lakes and through state forests. Just make sure you have low gears. Since you're just doing one overnight at a motel, you won't need to pack a lot.