
We Asked AI To Name The Snobbiest Cities In Massachusetts, These Were The Results
As a native of Massachusetts, certain cities may come to mind as potentially pretentious. They have that kind of atmosphere.
I asked ChatGPT about Massachusetts and its snobbiest towns. Some responses surprised me.
Indeed, this is all for fun, as many great people live in these cities.
Massachusetts's Snobbiest Cities
This is what I put in the ChatGPT prompt:
What do you think are the 10 snobbiest cities in Massachusetts?

Before going over the list, this is what was also said:
Massachusetts has a mix of historic charm, affluent areas, and bustling urban centers, so the idea of "snobbiest" cities can be subjective. Generally, these cities are often associated with wealth, exclusivity, and high-end living
And you know something, that's a perfect way to describe Massachusetts! Most of these cities have a rich history behind them, but have high costs.
So, here's what ChatGPT had to say about the 10 snobbiest cities in Massachusetts.
10. Cohasset
I have to be honest, I don't recall ever visiting Cohasset. But it's definitely on my bucket list now since ChatGPT says it's a beautiful South Shore town with high property values and a country-club lifestyle. I'm not interested in high property values, but a country-club lifestyle sounds like my cup of tea.
9. Marblehead
I wouldn't be surprised about this one since ChatGPT says it's a coastal town with historic charm, yacht clubs, and plenty of old money, it makes total sense.
8. Winchester
Any name with "er" at the end seems to mean business. ChatGPT says it's a small, exclusive suburb with a picturesque downtown and a high median income.
7. Cambridge
This one I was shocked. But again, getting an education is serious business. ChatGPT says that with Harvard and MIT, it's full of brilliant minds and an air of academic elitism.
6. Lexington
ChatGPT says it all. It's rich in history and wealth, with a top-ranking school system and a sophisticated feel.
I can't tell you how often I've driven by the now-closed Concord State Prison and thought, Is all the town has to offer? ChatGPT says it's home to a famous literary history and plenty of well-to-do residents.
4. Weston
ChatGPT says it's one of the wealthiest towns in Massachusetts, known for its sprawling estates and low-key exclusivity.
3. Brookline
Considering it's just outside Boston, those may or may not be surprised, depending on how you view this city. ChatGPT says it's a wealthy, urban suburb of Boston with an intense intellectual and cultural scene.
2. Newton
This one also surprised me, considering my relatives live in this area. ChatGPT says it's a highly educated, affluent suburb of Boston with historic homes and elite schools.
1. Wellesley
What's #1? ChatGPT says that Wellesley, Massachusetts, is home to Wellesley College and one of the wealthiest towns in the state, with top-tier schools and high-end boutiques.
That was Massachusetts. How about New York? Check out below:
The 10 Snobbiest Places In New York State
Here Are All the 2025 Concerts at TD Garden in Boston, Massachusetts
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This Massachusetts Home is Over a Century Older Than the Nation
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