Rail Trail

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.

This is a nice summer ride with lots of shade and an ice cream treat after lunch. Also, contrary to Cycle Club Rule #1 (There's always a hill after lunch), this ride takes the down-trending rail trail immediately after lunch! Keep the group fairly small so it won't take too long to get served at either Giovanni's or Louie's. If it's really hot out, stop at the Dunkin Donuts on Piermont Rd on the way home so everyone can get ice in their water bottles.

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.