UniChris

It's not as uniquely personal a question as it's being made out to be, I mean, sure I don't do well on extreme grades and am traffic cautious, but the reality is I do a lot of routes most who don't categorize themselves as serious road cyclists won't. In a sense, it's a more general form of the current Albany to NH with kids question.

Geographically, the CT coastline is a possibility I'm aware of, and additionally easy to access. Something just a few miles inland isn't obviously advantageous, though it happens I've explored a lot inland (good and bad) in the corner between the Thames and the RI line.

Something across CT further up, would be quite interesting - someday I'll try the air line though a Southeast Hartford-New London would be of more use than that northeast fragment of an NY-Boston train. Particularly interesting would be anything linking from the Farmington Canal west to NY's East-of-Hudson system that didn't go through the NYC metro area. Something I've been meaning to research more is Simsbury around the mountain to Hartford, with vague sights on Hop River and Air line or finding a way to parallel rt 2 to towards New London.

I'm relatively aware that little exists at a mid-Massachusetts lattitude, though if there's something I'm missing perpendicular to my countless CT river valley road rides...

I don't think it will happen this summer beyond an out-and-back from a parking lot, but anything through the White Mountains along the NH/ME line is interesting. Ironically my longest early-adulthood ride before I stopped cycling for 15 years was in the lakes region, its perhaps 15 miles now feels laughable but might try to head there again someday.