What is Connecticut’s Most Underrated Town? You’ll Never Guess

What is Connecticut's Most Underrated Town?

We all love an underdog. It’s why movies like Rocky and 8 Mile hit us right in the chest—there’s just something about rooting for someone the world overlooks, someone you can actually relate to. In Connecticut, we’ve got our fair share of “media darlings”—West Hartford, Mystic, Washington—but who’s our real Rocky? Which town is quietly crushing it without anyone really noticing?

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According to a new MSN article highlighting the most underrated town in each U.S. state, the honor in Connecticut goes to Guilford. Unlike its glitzy neighbors, Guilford has held onto its small-town charm. Nestled along the Long Island Sound, it’s home to the third-largest collection of historical houses in all of New England. Museums, taverns, inns, and centuries-old farms, this place has it all. It’s a town that proves you don’t need hype to be worth visiting—or living in.

Read More: The Most Expensive Town to Buy a Home in Connecticut 

Do I have a problem with Guilford getting some love? Not at all—it’s nice to see someone other than the usual suspects finally get recognition. But if we’re talking the most underrated town in Connecticut? Sorry, Guilford, you’re great, but you’re not the champ. That title belongs to New Milford. Convince me otherwise. You can’t.

What about our Tri-State neighbors? In New Jersey, it’s Keyport. Honestly, I can’t say I know a thing about it, so I won’t argue. But New York? Poughkeepsie. That one’s hilarious. I happen to know Poughkeepsie pretty well, and let’s just say… no. It’s rated, fairly. We can see the ratings, they're well-documented and accurate.