Sorry for the diatribe haha Based on the 5 CT towns I’ve spent significant time in as an adult, I’d have to say West Hartford has personally been the best experience. There’s a good sense of community, people seem to be more accepting. It’s fairly upscale and safe, but lacks the sting of snobbery. There’s comparatively more racial, cultural, and social diversity, the schools are good, and the downtown/blueback area has a lot going on. It’s a great place to raise kids, as most of the neighborhoods are very walkable and are set up in a way that seems to promote social interaction. The town radiates with opportunities for kids to grow up well rounded and learn life in a safe (but not insular) environment

Madison has great beaches (surf club and Hammonasset)… and that’s about it. Most of the residents and NYC weekenders have big time superiority complexes who are judgmental and obsessed with social status. The amount of 16 year olds bombing around town behind the wheel of their daddy’s Mercedes or BMW is mind blowing. The sub par downtown area is saturated with boutique shops run by bored, waspy housewives. The police force has had their share of scandals, including (but not limited to) lobster poaching, cocaine and hooker parties, and pimping teenaged prostitutes for backseat squad car romps. One officer had taken issue with me dating an ex of his whom he had repeatedly physically abused. He would literally stalk both she and I, and use “thin blue line” intimidation tactics. It was made clear to me that, after reporting his erratic and inappropriate behavior multiple times, his supervisor was complicit and flippant about the situation.

The high school educational experience is objectively good, and sports teams usually perform well. But if you care to look at what has been swept under the rug, you’ll find rampant opioid issues and teen suicides. Don’t ignore the fact that, for literal decades, the DHHS football program has heavily promoted steroid usage among players. Diversity is nil, as Madison is whiter than a mayonnaise and wonder bread sandwich, and it seems that most residents prefer it that way.

Guilford and Madison share many similarities, though Guilford is dialed way, way back. People are more relaxed and friendly, and are seemingly less concerned with what street you live on, or what car you drive. There’s a bit more diversity, the downtown green is top notch, and the schools are good. The biggest police scandal has been whether or not they should relocate the “open to the public” department’s basketball courts elsewhere.

I have lived in six different towns in CT, and while Madison was probably the wealthiest and was seemingly the “best town” on paper, my personal experiences there were pretty terrible. Look at the time, my free therapy hour is up haha