Crime & Safety
I like the fact that it's pretty small and you get to know a lot of the people well. There isn't a whole lot to do in Weston itself, but it's about 10 minutes from Westport, which has a lot of stores, 20 minutes to the beach, and an hour train ride to New York. It's also very safe: I've never heard of anyone having anything stolen or anything particularly crime-related occur. The public schools are very good and a lot of money goes into them. It's a big reason why people choose to live in Weston. If you do not have kids in the school system, it's harder to meet people, and may not be the best place for you to live. For the most part, people are friendly and it's nice to see your neighbors or people you know around town. I had a good experience in Weston, especially with the school system. It's very competitive and is probably more difficult than most schools in the US, but if you're looking for a quality education, Weston would be a very good choice.
I've lived in Weston for 20 years. Our children were educated on School Road. There is one over-arching focus in Weston - education of our children, followed closely by keeping a rural, community-caring tradition alive and well.
Weston, CT is an extremely safe and welcoming place to have grown up. Taxes are very high due to lack of industry in the town, but the school systems are among the top in the country. Though I did not go to private school, the Weston School system prepared me for college just as efficiently. The people are friendly, perhaps not as much so as those from the mid-west, but overall I have loved my time in Weston.