While outsiders may think of millionaires when they hear Connecticut (just like people think of Hollywood and Malibu when they hear California), the notion of it being a fabulously wealthy state is true only in a handful of towns in southwestern and central CT. While it is the richest state in the US, it also has two of the poorest cities in America--Hartford and Bridgeport. The few very wealthy people in CT are so incredibly rich that they skew the data, making the people of CT look richer than they really are. Go for a drive in Hartford, Bridgeport, Waterbury, New Haven, New Britain, or Willimantic as well as the rich places near NYC to get an accurate picture of the state. Connecticut people who live outside Fairfield County hardly even consider it to really be a part of the state--all they have in common with the rest of us is the design of their license plates.
Westport girl: I'm going shopping in The City this weekend.
Bristol guy: What "city"?
Westport girl: Why, New York! What other city would it be?
Bristol guy: Uhh, I have no reason to go to New York, so I rarely do. "The City" is pretty vague to people who are really from Connecticut and not just suburban New Yorkers.