Rail Trail

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.

This is an excellent way for strong C riders and slower B riders to do Bear Mountain. Take Metro North to Cold Spring. You start with a 10-mile warm-up ride from the Cold Spring train station and then do the 4-mile climb up Bear Mountain while you have lots of energy. After the descent there are still a couple of shorter climbs before lunch at the Cove Deli. Then it's mostly pleasant side roads and rail trail to get home, with a second snack/ice cream stop in W. Nyack. Ride ends on the NY side of the GW Bridge.