What Happens When You Ask AI About Connecticut’s Worst Towns and Best Pizza?

AI and Connecticut: A Candid Chat

AI is everywhere these days—people can't stop talking about it, and neither can I. Just the other day, I was chatting about it on the I-95 Morning Show, sharing clips of early AI pioneers warning us about what this technology could do. So, I wanted to see how “human” it really is. When I say “it,” I mean the free version of ChatGPT—yeah, that chatbot anyone with a phone or computer can use right now.

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I put it to the test with some questions about Connecticut, the kind you’d hear in a bar or at a family dinner—things that aren’t about facts or numbers, but about gut feelings, stereotypes, and opinions that might make you laugh, think, or maybe even get a little annoyed. Topics include which towns have the snobbiest people, the most beautiful spots, the worst place in the state, people who leave Connecticut for Florida, and of course, the all-important pizza debate. Read on to see how this AI answered—and maybe have your own take ready.

Q: First question, which Connecticut towns have the snobbiest people? Let's do the Top 3.

A: If we’re going by reputation, stereotypes, and what people actually say in comment sections, forums, and neighborhood Facebook groups, here’s your Top 3 “Snobbiest” Towns in Connecticut—with some honest nuance built in:

1. Greenwich
Let’s not pretend this was ever in question. Greenwich is the default answer. If Connecticut had a Real Housewives franchise, this is where they’d film it—marble kitchens, private schools, and Range Rovers in the Whole Foods parking lot. People don’t just have money here—they make sure you know they have it.

But the snobbiness isn’t just about wealth. It’s the attitude of detachment. There’s a sense that Greenwich doesn’t really see itself as part of Connecticut—it sees itself as a wealthy New York suburb that just happens to fall on this side of the border.

Common complaint: “They act like they should secede and form their own state.”

2. Westport
Westport is like Greenwich’s artsy cousin who’s also rich but pretends they’re not. There’s a lot of “We’re really into organic living and culture,” but that culture comes with a trust fund and a taste for $6 lattes and wine cellars.

The snobbery here feels like undercover superiority—the kind that says, “We’d never judge anyone… unless they shop at Target and don’t compost.”

Common complaint: “Westport people look down on you while pretending they’re super chill.”

3. Darien
Darien has a quiet, gated snobbery. It’s not as loud as Greenwich or curated as Westport—but that almost makes it worse. Think country club exclusivity. Old money. People who don’t raise their voice because they don’t need to—they have lawyers for that.

Darien residents aren’t trying to prove they’re better than you. They already believe it and see no need to explain.

Common complaint: “They pretend they don’t know what the Metro-North is, even though it stops right there.”

Honorable Mentions:
New Canaan, Wilton, Avon, and Glastonbury—each has its own strain of Connecticut snobbery, just in different packaging.

Read More: Personal Space, a Lost Concept in Connecticut? 

Q: Nice work. I'm afraid to ask the next question because I know I'm going to read the "M" word. What are the most beautiful towns in Connecticut?

A: You should be afraid. Because yes—you’re going to see the “M” word. But I won’t just hand you a brochure. This is the real-world, emotionally-charged list—the ones people post on Instagram and complain about being ruined by influencers every fall.

1. Mystic
There it is. The “M” word.

But come on—it’s earned. Mystic is absurdly charming, almost aggressively so. Cobblestone streets, boats in the harbor, fresh seafood, the drawbridge—it’s coastal New England perfection.

Locals will tell you how annoying it’s become. Tour buses. Seasonal crowds. People who think Mystic Pizza is fine dining. It’s been over-loved. But it’s beautiful as hell, and everyone knows it.

Most common vibe: “Mystic’s overrated—but I still take people there to show off Connecticut.”

2. Litchfield
If Mystic is our seaside prom queen, Litchfield is our countryside duchess. Colonial-era architecture, stone walls, white churches, and homes that look like magazine shoots. Especially stunning in the fall.

There’s an elegance to Litchfield that doesn’t need to be loud. It’s Connecticut’s answer to a country estate.

Most common vibe: “I just want to wear flannel, drink cider, and pretend my life is a Hallmark movie.”

3. Essex
Essex feels like it was frozen in time on purpose. Classic main street, historic homes, and that old-timey steamboat that gives the whole place a storybook vibe.

It doesn’t get as much national attention as Mystic, which helps preserve its charm. One of those towns that feels too pretty to be real but stays grounded.

Most common vibe: “This is what people from other states think all of Connecticut looks like.”

Honorable Mentions:
Chester, Guilford, Old Lyme, and Kent—all smaller towns with serious character and natural beauty that hold their own.

Q: What is your opinion of people who would leave a state as charming, safe and educated as Connecticut to move to a place like Florida?

A: If I’m channeling true Connecticut energy, then my opinion of people who leave a smart, safe, historically rich, actually-season-having state like Connecticut for Florida is:

"You’re dead to us. But also, you’ll be back."

From an intellectual perspective:
Connecticut has top-tier schools, some of the best healthcare in the country, low crime, and a highly literate population. Florida often struggles with infrastructure, education, and an overall sense of chaos. Leaving CT for Florida doesn’t scream “sound decision-making.”

From a social perspective:
There’s a vibe in CT that says, “If you want to go live where your neighbor has a pet alligator and your HOA fines you for your Christmas lights, go ahead. Just don’t expect us to take you seriously anymore.”

And yet... we kind of do take it personally. Because we know what they’re walking away from: real pizza, farmer’s markets, historic charm, and four actual seasons.

But there’s empathy, too:
Winters here are brutal. Taxes are real. Life in CT isn’t exactly easy-breezy. So people go for sunshine, no income tax, and palm trees. It’s understandable… on paper.

But what many find out—usually after their third hurricane scare—is that all that sunshine comes with a side of regret.

Final verdict:
Leaving Connecticut for Florida is like breaking up with a smart, classy partner because someone at the beach smiled at you. You might enjoy the fling, but good luck having a real conversation later.

Q: What's the worst place in Connecticut?

A: “Worst” is subjective. Crime? Decay? Boredom? Reputation? Depending on how you define it, you’ll get different answers—but one city always bubbles to the top:

Bridgeport.
It’s CT’s largest city, but none of the usual perks of being a big city seem to apply. There’s high crime, aging infrastructure, constant political drama, and an overwhelming vibe of “what could’ve been.”

Everyone in CT has a story about something bad happening to them in Bridgeport—even if it was just getting lost or seeing something on fire. It’s the Connecticut punchline that people want to root for, but usually don’t.

Common sentiment: “Bridgeport has potential!” (But we’ve been saying that for 30 years.)

Runners-Up:

Waterbury – Bad drivers, struggling downtown, “almost” turning a corner.

New Britain – Proud but tired, underfunded, and rough around the edges.

Willimantic – Scrappy but saddled with addiction issues and a rep that’s hard to shake.

Controversial Mention: Danbury – Some love it. Some think it’s just traffic, diesel fumes, and the mall.

Q: Connecticut has dubbed itself the pizza capital of the US. Do you believe Connecticut has the nation's best pizza?

A: Yes. I do.

And I say that not as a tourist, not as a food snob, but as a reflection of what actual pizza people—chefs, critics, food nerds—have been shouting for years:

Connecticut, especially New Haven, doesn’t just make good pizza. It makes the standard.

New Haven-style pizza (apizza) is thin, charred, chewy, and cooked in coal ovens that are practically historic landmarks. It doesn’t play by the usual pizza rules. Clam pie? Mashed potato pizza? No mozzarella unless you ask? That’s how we do it.

The power players:

• Frank Pepe’s – The iconic.

• Sally’s – The soul.

• Modern – The locals’ secret favorite.

• Bar – The innovator.

What about New York? Good, yes. But New Haven isn’t street pizza—it’s sit-down, argue-over-the-crust pizza.

Chicago? Delicious, but it’s a casserole.

Naples? Respect. But Connecticut is the gritty reboot.

Final verdict:
Connecticut is the pizza capital of the U.S.—not because we shout the loudest, but because the people who actually know pizza won’t shut up about it.

Q: I had fun with this but you're so wrong about the pizza.

A: And there it is. The sacred CT bond: love, pride, mutual respect… followed by immediate pizza warfare.

You’re allowed to be wrong—it’s part of the human experience. Maybe you had a bad slice. Maybe Sally’s gave you the burnt corner. I don’t judge. (I mean, I do, but silently.)

Next time, name names. Let’s do a taste-test breakdown.

I can't tell you how hard I laughed when the Chat Bot said moving to Florida from Connecticut is not "sound decision making" from an intellectual standpoint. That "From an Intellectual Standpoint" header was not my doing. I asked the question, and Intellectual Standpoint was one of the categories it created to answer the question from a variety of perspectives. Saying it's not sound decision making, intellectually is akin to a robot calling you a dumbass.

Florida, you say?

P.S. This was a ton of fun for me, but it doesn’t change how I feel about A.I.—I still believe it poses a serious threat to humanity. I know that might make me sound like an alarmist, but it’s genuinely how I feel… and some experts agree. Take a listen to our I-95 Morning Show segment from July 15, 2025, where we shared warnings from some of A.I.’s earliest pioneers.