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[quote=Anonymous][quote=Anonymous][quote=Anonymous][quote=Anonymous][quote=Anonymous]I think you’re forgetting the essential part of the town—lots of rich people and people without a real apparent source of income that nonetheless act like rich people.
For that, I vote Lenox Massachusetts.  Maybe great barrington.

There are also probably some towns closer to Boston (newbury? West newton?) or in New Hampshire (Durham?  Portsmouth?), in westchester (mount kisco?), or outside Chicago (highland park?).

If you want small town without the moneyed feel, there are lots more options, especially if you venture into more random parts of New England, maybe upper Michigan, etc.[/quote]

I didn’t get the sense that Gilmore girls boasted a town of rich people. Well, besides Lorelai’s parents. Lanes mom, single, owned an antique store. Luke owned the Diner but he was never fancy. None of the neighbors dressed fancy or acted rich. [/quote]

Lol. The homes in that town were huge. Where a single mother got the money to buy that beautiful old home is beyond me. They have unlimited funds to eat out every day.[/quote]

Stars Hollow absolutely isn’t supposed to be moneyed. It’s supposed to be very blue collar CT as that is how a single mom could afford it and why the school was “bad” and not good enough for Rory to go to a good college (even though I’m the poster who grew up in CT in that area and said it was likely a good school). Lots of central CT exist like this but don’t have the cute downtown area that Stars Hollow has.

I also always found it funny Richard and Emily are in Hartford. That makes no sense for a really rich person to live in CT and be surrounded by super wealthy folks. Hartford is not wealthy at all and not where the super rich people who would have maids and cooks live. Most of the moneyed CT folk live in Fairfield County.

I’ve clearly thought too much about this 😂.[/quote]

That house, even though it is supposed to be in a blue collar town, would be way out of a single mom’s budget. Mom was a maid at the inn and then moved up to manager. So unrealistic. [/quote]

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