New Haven to NY state line: Walking Route Help

[John Satterlee]

As part of a mid life crisis-I guess- I decided to walk my dog across the state of Connecticut. In sections, our general rule has been to try to link up parks, forests, land trust spaces etc with back roads as much as possible. With my route pretty set until I reach New Haven, I realize that I need help with a general route from New Haven to some point on the NY state line, not along the coast.

I have a couple of ideas I would like to run by someone familiar with the area as my familiarity with that part of the state is only from a handful of bike rides.

Does anyone happen to know anyone who can help me with route planning?

Thank-you,