Yes it is a wealthy town in Connecticut, but nothing compared to fairfield county. Contrary to what most believe, most residents do no flaunt there money, but some do. There are plenty of large expensive homes, but there are alot of small, medium sized homes. Many people do, in fact, have second homes (the cape, vineyard, vermont, florida) and many vacation any chance they get. But you have to understand that this is not the case for everyone in town. The stereotypical cheshire kid is polo popping and has a nice car, but again, its not everyone. College is big...very big. A schools reputation goes a long way in this town. Ivies and mini-ivies are common, but a ton of kids go to uconn. 98% of CHS students go on to college.Schools in town are very competitive, if u have a B average (3.0gpa) you almost always in the bottom half of your class.Parties are also a big thing because theres nothing else to do. BMWs, Mercedes, Lexus, Land Rovers, and so on are not uncommon, but there are plenty of chevys, fords, and jeeps.Snobbery is something you have to get used to, but not everyone is a stuck up. My point is is that cheshire is not filthy rich. There are plenty of average familys who work hard and live modestly. Its a great town.If you wanna see rich go to fairfield county.
Cheshires the place to be