Anonymous wrote:I live in Northern VA now but grew up in Weston and would recommend it over any of the other towns mentioned here. You get the quiet new england charm with the added bonus of having the hustle and bustle of Westport, Fairfield, Greenwich, Stamford nearby.

I should add - I would avoid Westport. It was and is still known for having an obnoxious, ostentatious vibe.

I live in Northern VA now but grew up in Weston and would recommend it over any of the other towns mentioned here. You get the quiet new england charm with the added bonus of having the hustle and bustle of Westport, Fairfield, Greenwich, Stamford nearby.

We moved to Weston from Westport (originally from DC with time in other large cities). Both are great and I would say Weston is to Westport like Potomac is to Bethesda. Rural but in a classy wealthy new england way. But still right near o all the amenities in Westport, Wilton, Fairfield, and Ridgefield. We preferred the smaller schools and tight community of Weston to Westport, and the large lots. But they're both great, just a matter of preference.

We skipped over Greenwich (too large), New Canaan and Darien (too much country club/range rover/blonde mom vibe).

Weird that this thread got revived after months. Not a CT expert. Darien and New Canaan are beautiful. But you are paying a premium to be closer to NYC, and it is all white Christians - almost no diversity - it is like a big Vineyard Vines commercial.

Westport has become much more diverse (big Jewish community) and is a bit further out so far from cheap but a little less.

Wilton and Weston are nice but feel more rural. Which has its pros and cons.

In Wilton there's a massive looming fiscal crisis - they have like $200M in deferred building maintenance and they propose to spend a measly $8M/year addressing it. And that's assuming they don't get a flood somewhere that suddenly forces them to spend a lot more money they don't have. There seems to be some realization that they need to expand their tax base, but not without controversy, and to be honest there aren't a whole lot of places to put them due to geographic / sewer capacity constraints - the largest new plot of development land to appear there in years is apparently going to be used to build yet another assisted living facility, which is not really the direction to go if you want to be a vibrant town.

(also, the schools aren't remotely what they're cracked up to be: a lot of meh un-fireable senior teachers who the administration refuses to take them on on stuff like 'actually teach our curriculum,' they abandoned Calkins only recently and with a lot of kicking and screaming, incredibly stingy budgets for anything but core academics, middle school theater is an outside nonprofit run by parents who - so I've been told - rig things for their kids, virtually zero leveling or other attempts to provide enrichment for smart kids, everybody with aspirations of going to an top-tier college has an outside tutor, they seem to have an ugly racism/swastika/whatever incident every year or so... just a mess in general)

Darien or New Canaan if you want small town, Greenwich if you want big. Greenwich is not as snooty as its reputation.

Anonymous wrote:Having lived in both Westport and Fairfield, I would choose Fairfield.

I loved growing up in Fairfield but if I had 3 Million to spend, I would live closer to the Stamford job.

Having lived in both Westport and Fairfield, I would choose Fairfield.

I grew up in Westport. Great schools, beach, main Street, train station.