http://www.ct.gov/dot/cwp/view.asp?a=1380&q=259662Not as good as the Rubels, but the CT one linked above is free.
Having ridden the ACA maps from new paltz to basically York Beach, in Maine, I would say that going north from CT to MA is not that hilly.. I've ridden to Great Barrington and have ridden north from there to Pittsfield and it's not a bad ride, some hills, nothing back breaking.
What is hilly is riding across Dutchess Cty on the ACA bike route, lots of rolling ups and downs. Just think millions of years ago, the glaciers flowed south from the polar regions of the north cutting valleys into the land (the Hudson Valley is a famous one, but there's also the Taconic and the CT river valleys). So basically, riding east/west across Dutchess is hilly while when you're heading north, it lessens.
The ACA maps across northern CT goes by a reservoir... forget the name but it's east of an American Legion State Forest campsite (we camped there). But I remember a big gradual uphill after that but nothing that isn't doable, i.e. you wont have to walk if you have the right gearing and endurance.
As far as riding east to New Haven.. Southern CT will be more dense than northern CT. The ACA route takes you all the way across CT to about the area south of Webster, MA (and that lake with the super long name :-) ). You could use those maps and then basically head north when you get to the Rt91 area around Enfield or so. However, MA is very pretty and probably more countrier than No CT. but less roads of course. NW CT is a very pretty part of CT in the taconics, the AT goes through there.
Jay
This message was edited by JayH on 8-23-06 @ 5:52 AM