Milford is my favorite one. One high school (Foran) is considered better than the other (Johnathan Law), but both are good. There's a train station to get you right to NYC, or to Bridgeport here in CT for events. I visited a lot growing up and I still do. Very nice city.

Shelton is close by. My current hometown. I love it here. You get the privilege of saying you live in Fairfield County for incredibly low taxes. I think the schools are seen as slightly less good than Milford, but they are still very good. There's a bunch of farms here. There's a also a train station to get you between Waterbury and Bridgeport. You can switch in Bridgeport for a train to NYC.

I grew up a town over in Trumbull. They have an amazing school system, a great music department, and great sports teams. The taxes are very high though, but if you want an expensive town with a great school system this is the one to choose. The really expensive ones such as Westport, Fairfield, Wilton, Darien, Greenwich, Easton, and so on are rip offs in my opinion. If it came down to it your kids would be able to apply to the agriscience program at Trumbull High someday. Milford high schools are good enough though. I know people with kids at Johnathan Law (the one seen as less good). No problems.

Overall I vote for Milford. Nice people, the mall, Dave & Busters at the mall, the movies, a train station with a train directly to NYC, but also stopping in Bridgeport for events, and a great downtown area.