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I used to commute from Stamford to Paramus. It was an hour. doable.
Trick was to get on the road really early. Coming home at times could be trouble in Westchester, but not always.
There seems to be a lot of Tappan Zee construction of late. I'd check as that would impact the commute. Eventually I moved to Nyack for year and my commute was so much nicer.
My last 4-5 years of commuting to Paramus I bit the bullet and decided to move to NJ (Ridgewood) and was quite happy. I was surprised that I ended up liking Jersey. But thats me.
You wanted info on the commute.. there you go, my commute from Stamford.
You do not want to go east of Greenwich as that part of the commute will be choked with traffic. So scratch New Canaan.
Since you asked about Ridgefield, it's possible from there that you could get to 684 without dealing with the Merritt/Hutch Parkways, but it's a lot of backroads (or going on rt. 35 which tends to have traffic) to get to 684.
I personally think that although you have your reasons and I'm not looking to probe, unless you're willing to accept the higher property taxes you might have to "bite the bullet" and live in NJ unless you want a very long commute. But if it makes you feel any better, I see quite a few NJ cars on my commutes into CT from southern Westchester (I work in different places each day between Stamford and Bridgeport) on both the Merritt and I-95 in CT, especially when I'm out early in the morning (6-7am) and usually from Norwalk on west, so I imagine people do the reverse as well. We're probably one of the few places in the US where some people cross TWO state lines on their commute. Good luck!