Anonymous wrote:

Anonymous wrote:At the end of the day Greenwich will always be Greenwich [Insert Darien or New Canaan or Westport] will always be fighting for second fiddle.

Why? Better downtown. Closer to NYC. Lower mil rate. Higher valued homes. I hear the public school argument, but only marginally so. Plus most people in Greenwich send their kids to Brunswick, GA or boarding school. I went to boarding school, class of ~80 I was only one from New Canaan, had 1 from Darien, probably over 20 from Greenwich. Point being if you’re moving to Greenwich you don’t care if your public schools are 8/10 and Darien/New Canaan/ Staples are 9/10.

Darien/New Canaan/Westport embody 1st/2nd generation New Money. Greenwich is more 3rd/5th generation. They’ve moved past the need to flash and generally speaking more concerned with future generation wealth preservation, even at the expense of the current being “cheap.”

This will trigger many, it’s entirely true though. Rich people in London and Paris may have heard of Greenwich CT because it’s a luxury brand. Darien isn’t, it is ex DIII lax dads coaching little league after their second DUI and fourth sales job in as many years. It’s not the same.

Hmm that is so interesting! When did you live in Greenwich, and how many generations has your family been there? I grew up there in the 90’s but towards the end before I went off to college I felt like it was really going off the rails. Overly-glossy Russian snobs in Lilly Pulitzer, farmland and old houses being chopped up and replaced by ugly pretend-colonial monstrosities (obviously nothing as bad as what now burns my eyes daily in Northern Va). There was plenty of new money mixing in at the privates, and the people w the richest or most famous parents tended to lead the pack. Even the quiet, older families had allll sorts of issues and bad values like half-siblings of the same age being the norm, totally absent parents leading to some pretty awful pushing of the envelope in middle school etc. I had always romanticized some of the other surrounding towns as low key, relaxed antidotes to gleaming Greenwich…less pretentious, less clout-chasing, but probably more parochial, less diverse. Darien especially seemed really appealing, since I was a horse girl and still am one at heart.

Anonymous wrote:I would not pick Westport, beautiful town but much more emphasis on conspicuous consumption and flashy wealth. There is some of that in all the mentioned towns but Westport definitely has a reputation. I would pick Greenwich in a heartbeat, great downtown area, much more international, cosmopolitan vibe, good choice of public and private schools, beaches, parks, shopping and better commute to NYC.

As someone who grew up in Westport, I do not think it is "flashy" wealthy. My family is still there, and I visit a few times a year; Agree that is flashier than when I grew up there ('80's) but still not, in my view, considered to be "flashy," but more understated.

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:New poster here tuning in. I'm considering a job in Stamford. Is it a reasonable commute from Wilton or New Canaan?

Personally I would just live in Stamford.

No. Do not live in Stamford unless you are in your 20s.

- Lived in Stamford.

Plus 1

Grew up in westport, and I agree

I would not pick Westport, beautiful town but much more emphasis on conspicuous consumption and flashy wealth. There is some of that in all the mentioned towns but Westport definitely has a reputation. I would pick Greenwich in a heartbeat, great downtown area, much more international, cosmopolitan vibe, good choice of public and private schools, beaches, parks, shopping and better commute to NYC.