BlaRo
Little Nudger
These CT routes are cool too since you can hug the coast and see nice views of the sound, and do some mansion gawking too.
What roads would you take for that?
I've been up to Bear Mountain before, following 9W past Nyack isn't very far and has entertaining elevation changes. But there really are a ton of Sunday drivers as it's a busy road, 4 lanes in many places.
Greenwich along the coast up to Westport, then north to Redding and west to Bear Mountain? I really don't know CT roads, or specific roads in general, and MA's roads are always busy as hell.