If the Trader Joe’s/Whole Foods aspect is super important to you then I’d look in the Orange/Milford area as CT doesn’t have that many of those particular chains but they do have them in that area!

If it’s less important then I’d recommend Guilford. My husband grew up there and they have a great school system, very safe, and there’s a train station in town. Only about 30 minute drive to Yale.

We currently live in Hamden now in the Spring Glen/Whitneyville area. We love it for now, however, I’ve heard the high school is just okay and we’ll likely move when we have kids.

My husband happens to be a realtor who works with a lot of incoming Yale staff. Yale often will connect people moving to the area with possible realtors who are very knowledgeable and can help you look at the best spots. My husband takes people of tours of towns all the time which I think helps give a good feel for the area. May be worth connecting to the hiring team to see if they might offer that to your wife!