My old hometown of Trumbull is 72, my current hometown of Shelton is 81, and my side hometown (because I have a lot of family there) of Milford is 99.

I would have put Milford higher. I love living in Shelton, but if I could afford it I'd be in Milford. I don't have kids, but there's great schools for people that do, there's beaches, a mall, a movies, a great downtown, and a train station that gets you directly to New York.

Shelton has a train station at Home Depot called the Shelton/Derby stop, that gets you to Bridgeport, and then you can switch to an NYC train. I'd rather have a direct train stop though.

Trumbull is very nice, and I was lucky to live in a safe place, but the taxes are horrendous, and both Shelton and Milford offer more to people of all ages. Milford more than Shelton though.