
The 10 Snobbiest Cites In Massachusetts According To AI
As a Massachusetts native, there are some cities that will pop up in your mind of which ones can be the snobbiest. They just have that type of vibe.
I went ahead and asked ChatGPT what it thinks about Massachusetts and what could the snobbiest towns possibly be. While some of these came all back to me, but some actually caught me by surprise.
Of course, this all for the fun of it as many great people do 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 do have a rich history behind them with a high cost that comes with it.
Read More: Narcotics Worth Over $35,000 Seized In This Massachusetts City
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. Not that I'm interested in high property values, but country-club lifestyle sounds like my cup of tea.
9. Marblehead
This one I wouldn't be surprised since ChatGPT says it's a coastal town with historic charm, yacht clubs, and plenty of old money it makes total sense.
8. Winchester
It seems like any name with "er" at the end means business. ChatGPT says it's a small, exclusive suburb with a picturesque downtown and high median income.
7. Cambridge
This one I was really shocked. But again, getting an education is serious business. ChatGPT says 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 many times I've driven by the now closed Concord State Prison and thought to myself, is all the town has to offer? Nope, ChatGPT says it's home to famous literary history and plenty of well-to-do residents.
4. Weston
ChatGPT says it's one of the richest towns in Massachusetts, known for its sprawling estates and low-key exclusivity.
3. Brookline
Considering it's just outside of Boston, those maybe surprised or not surprised depending on how you view this city. ChatGPT says it's a wealthy, urban suburb of Boston with a strong intellectual and cultural scene.
2. Newton
This one also caught me by surprise considering I have relatives that 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 Wellsley, 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
Gallery Credit: Sean McKenna
This Massachusetts Home is Over a Century Older Than the Nation
Gallery Credit: Lizzy Snyder
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