Spoken like a true Long Islander, *****ing about the hills !. Just kidding you Tom !. I agree with you. There's a long uphill on the NCT off the reservoir to Yorktown, then 3 or more miles of steady uphill grade from north of Yorktown to the Putnam County line, that always wears me down.

AFAIK, Brewster is as far as Putnam County plans to go and can go. When you hit the northern end you are at Putnam Ave. at Rt 6. If you head east on Rt 6 for exactly a mile, you come to the Brewster Metro North station.

I had read that there were/are plans to use the rail road bed that goes from North Brewster to Danbury, on an un-used railroad that parallels I84, but plans are on hold as nobody over in Connecticut has shown an interest. There is no easy way to link the Putnam extension of the NCT to the Danbury section, as the Putnam section goes pretty much as far as it can currently. Metro North still uses a 1/2 mile section of the Old Put RR as a storage yard in Brewster. So any links to other Rail Trails would need to be on-road for a bit.

As BTW, the Danbury to Brewster RR was known as the "New York and New England RR" and heads west from Brewster (it does not join with Metro North) across Putnam to Poughkeepsie and is is the railroad that cross the train bridge on the Hudson. I believe this is supposed to link to the Walkill Valley Rail Trail. That would be a hell of a ride !.