Anonymous wrote:Grew up in Darien, parents and later I worked in Stamford, Greenwich, and Norwalk. My parents made wonderful friends in town and the beaches are great, but we often felt very uncool and excluded because we weren't as wealthy as most. I grew up on the "wrong" side of town next to the Stamford border, smaller houses and properties. Elementary school was great because everyone else was in similar situation - but then we got to middle school and met all the rich kids and it was a piranha tank. Everything was extremely competitive, particularly in sports - these are the kids of top executives and the best at everything, and nowadays they have private coaches and clubs, and it's even harder to compete. Even in the 1980s, you could be a mediocre swimmer in Darien and if they plopped you down pretty much anywhere else in the country, you'd be winning like crazy. If you are not good looking and/or athletic, it's hard, and even if you are, it is a pressure cooker.
None of us moved back there with our families as adults. Even if we could afford a $700K 3br 1ba starter house next to the Turnpike or the train tracks, we don't want our kids growing up in that level of competition and all the emphasis on money. If I were going to live anywhere on the Gold Coast, I'd pick Fairfield. Still great schools but people seem more normal there. My sister lives in backcountry Fairfield County (Monroe/Ridgefield area) and it is much more down to earth. Some of my classmates stayed in Darien. They were popular rich kids then and are popular rich adults now. Some married other townies.
Tokeneke...most of it falls into the private Tokeneke Association. It's not gated but is private, they have their own police force and it's extremely upscale and very quiet. There is a private beach club that costs a lot to join, but no public beach or waterfront access (unless your house happens to have such). However, there are parts of the Tokeneke elementary school district that are not in the Association.
Greenwich is nice, I would argue more diverse (there are housing projects and non-Christian houses of religion) but still very wealthy and competitive. The high school is huge but good. There are a lot more neighborhoods to choose from. Greenwich has a much better downtown that Darien, which has struggled to keep a single small movie theater going - Darien is a long strip that developers have tried to redo and now it looks all unrecognizably pretty but people still don't go there. I agree with a PP that Darien has better beaches, but I say Greenwich has better parks. The best local downtown is probably New Canaan though.
For the person talking about commuting to Stamford, go with New Canaan, not Wilton. You would be less dependent on highways, which are a mess at rush hour and often at other times. You could either take the back roads or the Metro-North New Canaan spur. Wilton is also just hard to get to. They have a spur too but it is further out and less direct. You could also try Silvermine, it is a great artsy little neoghborhood where New Canaan, Wilton, and Norwalk conjoin - you'd get the benefits of New Canaan but more character and less hedge funds.
fewer
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