Anonymous wrote:Westport might be friendly if you grew up there and your family has roots there. Coming in as a family of outsiders (with not even an acquaintance) is not so pleasant, and I speak from experience!

I have to agree- I spent a good portion of my childhood there and while I do have some great friends to this day it was not an easy place to live as a child without means. The schools are great (why my parents moved there) and I had a terrific education that has served me well. Yes, most people to go to public school- GFA is pretty small and there are a few private schools in Fairfield.

I think there 's even more $ there now (or at least showy money). So many of the homes I once knew have been demolished and or renovated and look nothing like they once did.

Other cons: It's not very diverse in terms of economics and race.

Despite all of this, there are many many great perks- Longshore, the beaches, Westport Country Playhouse, shopping downtown, train to NYC, etc.


I'll have to check out that donut shop mentioned above- I've never heard of it before.

"Yankee" is deragatory? I found her use of it to be rather charming.

My grandparents lived in Weston, and that area is one of my favorite places.

you are sooooo lucky.

Anytime you move anywhere there will be insular people, OP. I would not use the word Yankee, as it is derogatory and makes you sound uneducated. CT is beautiful and there is much to enjoy, if you let yourself. I am jealous! GL.

Do most Westport kids go to the public schools?

I spent HS years near there. I would say it is not particularly welcoming to outsiders and the less-affluent. I have family in New Canaan and I hate visiting up there. It's pretty in the fall, but all their roads and narrow, houses are spread out with no sidewalks. Although I house-sat for some families who lived on water in Westport. Those homes were very small and close-together, but seemed like a nice area.

And my favor clothing store is Henry Lehrer. $$ but great.

Westport might be friendly if you grew up there and your family has roots there. Coming in as a family of outsiders (with not even an acquaintance) is not so pleasant, and I speak from experience!

Coffee An'. On N. Main. President Clinton used to have them delivered to the white house. It is basically a coffee shop with average food but The DONUTS have been written up, and are delicious. Hole in the wall place.

PP here.

I find Westport welcoming, friendly. The town did not like Martha Stuart because SHE is unfriendly, and did not fit in because of that. Paul Newman lived there for most of his life until his recent death, and he used to publicly comment that he chose Westport because it was friendly, not stuck up.

Anonymous wrote:I grew up there, and parents are still there, and I visit often. It is an affluent, coastal community. It prides itself on being an artistic community, and provides cultural opportunities. Very charming. Many beautiful old homes, and some ugly McMansions, unfortunately. 1 hour from NYC. Good shopping, and the best donuts in USA. Liberal, suburban, casual, unpretentious. 25,000 people. You are lucky to have this opportunity. Take me with you. Good schools. Hope this helps. Let me know if you need more info, details.

Where are these donuts of which you speak?

I grew up there, and parents are still there, and I visit often. It is an affluent, coastal community. It prides itself on being an artistic community, and provides cultural opportunities. Very charming. Many beautiful old homes, and some ugly McMansions, unfortunately. 1 hour from NYC. Good shopping, and the best donuts in USA. Liberal, suburban, casual, unpretentious. 25,000 people. You are lucky to have this opportunity. Take me with you. Good schools. Hope this helps. Let me know if you need more info, details.

First of all, Westport is absolutely beautiful. I'm not going to lie, it is not a warm, welcoming place (Martha Stewart fit in there for a reason!) but once you're settled and you find your niche you should be fine. It's expensive (even by our standards) but it's worth it as the schools are great, it's relatively safe and there are great restaurants, shopping and the beach.

Good luck to you! Are you set on Westport? Some of the surrounding towns are very nice, too. I really like Easton and Weston, or maybe South Norwalk if you're looking for something a little more down to earth.

DH just got a job offer, and we might be moving there. Living in D.C. is the farthest north we've ever lived. What would it be like living in that Yankee town?!