Once upon a time there were trains and busy train stations in The Catskills (Old Postcard of Loch Sheldrake Train with a romantic couple.)
The Quickway opened and Brooklynites hopped into their cars for the long drive to their bungalows. The Queen of all rest stops, The Red Apple Rest, was the halfway mark in Tuxedo, NY. The Red Apple is to be reopened someday they say. I spoke to a contractor who said he was hired to start working on the place in a few months (early spring 2009.) There have been some repairs done to the roof just to get it through the winter months.
The Tuxedo Metro North Train Station is almost finished being renovated. The train is on the Port Jervis Line, see maps of train lines here.
Getting to a place like Loch Sheldrake from Manhattan would mean you'd get as far as Middletown, NY and then have to rely on a bus. Hopefully the line will extend one day from Middletown up to Roscoe. They could call it the Fly Fisherman's Flyer.