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!
Anonymous wrote:Westporter here. ....train ride from westport to grand central is 1 hour
Anonymous wrote:I grew up in Westchester, NY, and have several friends from there who now live in Westport. I LOVE it. I've always found it warm and friendly - much more so than DC.
I wish I could move back up there. OP, you're very lucky!
As for the term Yankee, I don't think too many people think of southern CT as Yankee territory - unless you're talking about baseball. All of my friends from Westport commute to Manhattan for work every day. So, they're more metropolitan/New Yorky than Yankee.
Anonymous wrote: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?!

Anonymous wrote: Connecticut is one of the New England states and there is no way in hell it could ever be considered southern.
Anonymous wrote: Really? You get uptight about Yankee? This is a new one for me too. And I'm from there. I know some terms can move into truly derogatory territory, but I didn't realize Yankee had gotten there.