Why Massachusetts’ And New York Snobbiest Towns Still Have Great People

As a resident of Massachusetts, I sometimes perceive certain cities as pretentious.

I was taken aback by the responses I received about the snobbiest towns in Massachusetts.

This is all meant to be lighthearted, as many wonderful people live in these cities.

The Snobbiest Cities in Massachusetts

I included the following text in the ChatGPT prompt:

What do you think are the 10 snobbiest cities in Massachusetts?

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Before reviewing the list, it’s important to highlight what was previously mentioned:

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

Massachusetts is aptly described this way: many cities have rich histories, but they also face high costs.

Here is a summary of the ten most exclusive cities in Massachusetts.

10. Cohasset 

I have to be honest—I don’t recall ever visiting Cohasset. However, it has definitely made it onto my bucket list now, as I’ve heard it’s a beautiful town on the South Shore with a country-club lifestyle. While I’m not especially concerned about high property values, the idea of a country-club lifestyle sounds appealing to me.

9. Marblehead

I wouldn't be surprised by this, as it describes a coastal town with historic charm, yacht clubs, and old money; it makes total sense.

8. Winchester

Names that end with "er" often imply a business context. ChatGPT describes it as a small, exclusive suburb with a charming downtown and a high median income.

7. Cambridge

This was surprising to me. However, pursuing an education is a serious matter. At Harvard and MIT, there is a wealth of brilliant minds and a sense of academic elitism.

6. Lexington

The area is renowned for its rich history and affluence, boasting a top-ranking school system and a sophisticated atmosphere.

5. Concord

I often drive by the now-closed Concord State Prison, wondering if this is all the town has to offer. It is known for its literary history and affluent residents.

4. Weston

It is regarded as one of the wealthiest towns in Massachusetts, recognized for its vast estates and subtle exclusivity.

3. Brookline

Given its proximity to Boston, reactions may vary depending on one's perspective of the city. It is known as a wealthy urban suburb of Boston, boasting a vibrant intellectual and cultural scene.

2. Newton

This surprised me, especially since my relatives live nearby. It describes the area as a highly educated, affluent suburb of Boston, featuring historic homes and elite schools.

1. Wellesley

Wellesley, Massachusetts, is known for Wellesley College and is one of the wealthiest towns in the state, featuring top-tier schools and high-end boutiques.

That was a brief overview of Massachusetts. Now, let's turn our attention to New York.