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.

Anonymous wrote:The Byram neighborhood of Greenwich has a lot of diversity. I have interviewed several housekeepers over the years that live in Byram. Their kids go to Greenwich public schools. People don't really how huge of an area Greenwich is. It covers a lot.

A minority does not equate with "diversity". That's always been the case of Byram. When I was at GHS in the mid 80s we had a student population of 3000 and of that maybe 10 AA kids 10 Japanese/ Chinese kids and 20 Hispanic kids.

The Byram neighborhood of Greenwich has a lot of diversity. I have interviewed several housekeepers over the years that live in Byram. Their kids go to Greenwich public schools. People don't really how huge of an area Greenwich is. It covers a lot.

Greenwich is not diverse at all. Nearby Stamford is diverse.

Anonymous wrote:

Anonymous wrote:Darien is a small town. Lots of people who live there also went to high school together. Greenwich is more diverse.

HAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHA.

I'm sorry - did you just say Greenwich is diverse?

HAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHA.

It is, especially when compared to Darien.

Darien was once a "sundown town"--look it up. I wonder if that has changed. I grew up nearby.

Anonymous wrote:Greenwich is a "bedroom community," meaning it is full of NYC commuters.

Darien would have more (not all) people whose lives are centered in CT.

What do you plan? Do you want to go into the city often or live a more suburban existence? Also, if you plan to travel to New England often, the further you can start from NY, the better.

Old Greenwich and Riverside are not bedroom communities. They are full of families taking advantage of the local schools. And lots of old money. And Catholics and Jews. Something for everyone!

Anonymous wrote:Darien is a small town. Lots of people who live there also went to high school together. Greenwich is more diverse.

HAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHA.

I'm sorry - did you just say Greenwich is diverse?

HAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHA.

Greenwich is a "bedroom community," meaning it is full of NYC commuters.

Darien would have more (not all) people whose lives are centered in CT.

What do you plan? Do you want to go into the city often or live a more suburban existence? Also, if you plan to travel to New England often, the further you can start from NY, the better.

I wouldn't say Westport is down to earth, but the beach is nice and the schools are great and there is an active Jewish community

Anonymous wrote:If you are Jewish, don't move to Darien

Yup. Aryan Darien

Anonymous wrote:New poster here who is also thinking about Darien vs Greenwich... but also considering Westport. I know that Westport is a longer commute, but outside of that -- what is the town vibe like? My husband and I are Jewish and from DC, but we both went to Amherst and I played soccer and ran track in college (so we are comfortable with New England WASPS and I am familiar with crazy suburban sports parents... husband works in television and I work in finance).

We're not interested in keeping up with the Jonses or having amazing dinner parties. We just want to live in a place where people are somewhat down to earth and there aren't too many sharp elbows.

You'll like Westport. My sister and BIL who went to Williams and played soccer there love it. And we (I played tennis at Williams and DH went to Michigan) love to visit them.

I have lived in both Darien and Greenwich and both are excellent towns that have quite stark differences despite seeming like having so much in common.

Major points of similarity:
-Both are very affluent towns
-For work, both have an emphasis on finance (particularly buy-side), although this is even more apparent in G'wich
-Good school systems
-Access to beaches / LI sound (although Darien is decidedly more "beachy" and both Pear Tree and Weed Beach are nicer than Tods Point, IMO)
-The club scene is big in both towns, notably country clubs (there are 3 in Darien and like 7 in Gwich) but also beach, racquet and yacht clubs

Major points of difference:
-The upper-end wealth in Greenwich is in a different stratosphere than almost anywhere else in the country, Darien included
-Greenwich is WAY bigger and, IMO, doesn't have a "town" feel; you tend to socialize with circles based on neighborhood (e.g., OG, Riverside, CC, etc.), club (country clubs, yacht clubs, etc.) or kids' school
-Speaking of schools, most kids in Darien go to the local public schools, there is far more private school participation in Greenwich (notably because Darien doesn't host any private schools, Greenwich has them in abundance... Brunswick, GCDS, GA, Sacred Heart, Greenwich Catholic...)
-As others have mentioned, I've found Greenwich to be far more diverse / cosmopolitan while Darien feels like being back in prep school / college.... it's not for everyone but I like it
-More going on in Gwich... strong restaurant scene, Gwich Wine and Food festival, Greenwich Concourse, Greenwich Film Festival... although most of these are available to non-Gwich residents (Town Party might be the exception) so if you live nearby it doesn't really matter

Anonymous wrote:Westport is a 45 mins drive from Old Greenwich, in the opposite direction of Manhattan. Old Greenwich is something like 30 mins on the train to Grand Central.

Do you want to spend your entire life commuting?

What are you talking about!!
Old Greenwich to Grand Central is 1h13m
Westport to Grand Central is only about 10m more

If you are driving from Old Greenwich to Westport it does not take you 45minutes!!! It is 15 minutes assuming you are not going during rush hour. Even from Greenwich proper it would take maybe 20minutes.

Greenwich is on exit 2-3-4 of I95
Cos cob is on exit 4
Riverside and Old Greenwich exit 5
Darien is on exit 11-12
Westport exit 18

-I live in Guilford (exit 58) and it takes me exactly 55 minutes to get to Greenwich (every day!)

Anonymous wrote:What about Larchmont, NY?

ugh start a new thread, dude.