[conway234]

Westport and New Canaan are both very nice but expensive places to live. I used to live in New Canaan but moved for various reasons. My family had a difficult time fitting in, but everyone's experience is unique. I am happy to explain off line.

Both towns have great public schools, and great town centers. Westport will have more chain stores than New Canaan. And likely fewer empty storefronts. NC has more mom and pop shops. Westport also has beach access where NC does not. In terms of politics, NC used to be more republican and still slightly leans that way. Although many of the younger arrivals to town have leaned more leftward. NC used to be the lone republican holdout in lower Fairfield County, but that has been changing. The first selectman election a few years ago was narrowly won by the republican whereas in prior years it wouldn't have been much of a contest. The 2016 election titled in favor of Hillary and 2020 was even more in favor of Biden..granted Trump is unique. But in 2012, Romney won with close to 70% of New Canaan's vote.

Westport has always been more liberal. You'll find more of the Massachusetts/New England liberal types in Westport than in NC.

I find neither town as "down to earth" as someone mentioned. Private clubs are a big thing in NC. Since you are coming from Montclair, an area I know well, you might find you like the vibe of Westport a little more. I think it is more of a mixed bag than NC. Send me a PM if you want more info.

[Route7toRoute202]

Originally Posted by BPt111

People are more down to earth in New Canaan than Westport.

Either way, neither towns are down to earth at all.