New Rankings: The Top Three Snobbiest Cities in Maine in 2025

When you think about our Pine Tree State, your first thought probably isn’t that it’s filled with ‘snobs’ or that our cities are necessarily ‘snobby.’

Here in Maine, we’re a hardworking, nose-to-the-grindstone bunch who take pride in earning what we have and appreciating it—without looking down on others. But let’s be honest, somewhere has to be considered the ‘snobbiest,’ and while that doesn’t necessarily mean they’re truly snobby, this list shows which towns wear that metaphorical crown.

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That said, how exactly do we know—or at least, how do we decide—which cities make the list, and what qualifies them as the three 'snobbiest' in our state?

To find the snobbiest cities in Maine, we turned to ChatGPT and asked it to rank the top three based on what it interprets as making one place more ‘snobby' than another.

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The artificial intelligence’s ranking was based on things like high home prices, plenty of white-collar or degree-heavy households, and a general ‘we curate our lifestyle here’ vibe.

It also factored in status-focused amenities like yacht clubs and boutique dining, along with stricter rules and regulations, and made sure to note that the word ‘city’ is used pretty loosely for this ranking, because, well… Maine.

With that established, which cities in Maine ranked as the snobbiest in all of Vacationland, at least according to AI, in 2025?

Again, it’s worth repeating—artificial intelligence made these rankings, we’re just the messenger. And we’re pretty sure there’s a saying about not shooting the messenger, so if you’re offended by this list, either don’t be... or take it up with the AI, not us.

Falmouth ranks third thanks to its high incomes, prime waterfront, golf and yacht clubs, and quick access to Portland without actually being Portland.

With pricey homes, exclusive memberships, and a ‘rules-forward’ vibe, it’s less touristy than some places and less iconic than others, yet still carries a quiet, confident snob factor.

Coming in 2nd place, Kennebunkport mixes old-money summer colony charm with luxury inns, art galleries, and plenty of yacht-club prestige.

The artificial intelligence says it’s a polished, resort-town kind of posh—from the Bush compound to high-end boutiques—that’s both curated and costly.

Ranking as the snobbiest city in Maine, Cape Elizabeth earns the top spot with its pricey coastal homes, excellent schools, and quiet, residential vibe.

ChatGPT says it’s the kind of place where status is shown in Teslas, pristine lawns, and understated New England charm rather than anything flashy.

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And there you have it—apparently, the top three snobbiest cities in Maine for 2025 are Falmouth, Kennebunkport, and Cape Elizabeth.

What are your thoughts on these rankings? Do you think artificial intelligence got it right? We’d love to hear from you! Feel free to join the conversation by messaging us on the app.

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