Your initial idea of the Harlem Valley and Hudson Valley is excellent. The quiet roads thru the farmland nearby are even prettier than the Harlem Valley Rail Trail. Like there's a
19-mile route which combines both the rail trail and the nearby roads. And here's a
29-mile route thru wonderful farmland in the same area including Sharon CT.
The northern section of that Rail Trail is shorter but prettier than the southern, and also has
riding on great farmland roads nearby. (Surprising to New Englanders: most of that Harlem Valley area drains to the Housatonic River.)
If you're into rail trails, less than an hours drive is the new Walkway over the Hudson, supposed to be the longest bridge open only to cyclists and walkers in the world. It really is pretty remarkable to ride across.
Sharon and I were riding in a different area of the Housatonic River just yesterday, around Canaan CT and Sheffield MA. The 28-mile variation of the southern part of this
southern Berkshires loop has a wonderful concentration of farmland on quiet roads -- saw lots of other people out riding, with few cars. So making a base around there could be good, but I think there's a larger concentration of pretty "New England style" roads + rail trails around Copake NY -- or Millerton NY is like 12 miles on the main road from Canaan and right on the rail trail.
southeast Rhode Island might be another area to check out for for quiet roads thru farmland. Neaby is the notably pretty East Bay bike trail.
The Champlain Valley (west side of VT) and Hoosic R area (northwest MA) also have some nice farmland opportunities, but my experience is that there's a bigger concentration and higher percentage of real farms with cows + horses a bit further south in that same corridor:
Columbia county [
route ideas] and northern Dutchess county in the Hudson valley of NY. (within an hours drive of the Harlem Valley Rail Trail). Why it's better further south:
- more roads paved. Therefore more of them available to carry the heavy traffic, so more roads "left over" for cyclists who prefer little traffic.
- better paving + wider.
- more roads that are not ridiculously steep.
- farmers seem to like it better where it's a little warmer - (perhaps historically VT had more farmland, but now lots of that has reverted to forest and vacant fields with residences).
- better food stops, because close to the Culinary Institute of America with newly graduating chefs looking to open a little place to get started.
- better food stops, because of weekending Manhattan folks with money to spend on more "creative" snacks and support multiple food spots in one village.
Ken
P.S. Hilly ...
not sure where your coming from, but it's difficult to find pretty riding on quiet roads around New England and the Hudson Valley without running into hills. But many of the climbs lead to big views and fun downhills, so Sharon and I have decided that it's worth it to patiently climb in our lowest gear, or even walk a short steep section.