The root of the problem is local property taxes that get funneled into local school districts, which then become known as the best district, which drives up the local housing prices, etc. It's all a feedback loop. We have no way of knowing if the instruction in New Canaan or Darien schools is actually good. When nearly all of the kids have wealthy parents that both have at least Bachelor's degrees (and in many households, both parents have advanced degrees), those students will do well regardless of the schools. I don't have an easy fix to propose, but honestly I wouldn't want my kids to grow up in these towns or go to these schools (we live in Stamford and kids go to Stamford public schools). They're little hothouses for wealthy, entitled people whose kids are all stressed out about being successful, and these kids leave school rarely having interacted with someone not like them.