US 44 between Millbrook and North Canaan is a beautiful route any time of year. It's sort of a trip to the past as one drives through the little communities that time left behind. With the exception of a few convenience stores, you won't find any retail chains in Millerton, Millerton, Salisbury, etc... just old-fashioned hardware stores, original diners, little B&Bs. It's charming. These villages are very interested in maintaining that aesthetic by controlling who can open up. With the new rail trails, hiking trails, state and local parks, and other attractions along that corridor, it's a pretty under-appreciated part of the region IMO.
I've been in Millbrook 19 years now and it's the same as it ever was. Quite literally indistinguishable from 2001 in almost all respects. I find it comforting in a way.