Stamford is a city as are other Connecticut cities e.g. Bridgeport, New Haven, Waterbury, Danbury, Norwalk, Hartford, etc. Other places like Greenwich, New Canaan, Wilton, and Westport are towns. Running a City schools system is much different from running a town school system due to many factors e.g. size obviously but also a larger number of schools, more transportation issues, ranges of families' economic status, larger number of non-English speaking families, larger number of families with parents who don't have a college degree etc.

On the plus side, the populations are much more diverse. I referee soccer games ages U12 to U17 and there is definitely a different entitlement attitude with kids from Darien/New Canaan, etc compared to Stamford or Norwalk kids.

My kids went thru the Norwalk school system which has its problems. But with my last now in his senior year of college, I have to say they had a great experience and I wouldn't change anything if given a choice. They are well-rounded kids with humility, got into great colleges and my older two have successfully started their post-college careers. We were involved a lot and we definitely pushed them to be what they can be so in my opinion it's important to be engaged with them and their schools without being overbearing.