2022’s Most Fun Cities in America

Predictable. I think we all know you can have fun in Vegas, Miami, Orlando, The Big Apple, The Big Easy, and Austin.

By the way, Madison is underrated. It is a way more fun place than Milwaukee or Rochester, which are rated higher on the list. (Those are three places where I spend a lot of time.)

But the more interesting question is “Where can you have the LEAST fun?”

America’s most boring places include:

South Burlington, Vermont
Oxnard, California
Yonkers, NY
Laredo, Texas
Lewiston, Maine

6 thoughts on “2022’s Most Fun Cities in America

  1. Cincinnati??? That high???? There isn’t much to see or do there. Feels like you’re in Kentucky. It frequently listed as one of the worst road trip cities among pro athletes because there is so little to do.

    I lived in Wisconsin for seven and a half years. Madison is the quintessential good time college town. In all those years there were still places I never got to. Milwaukee isnt bad.

  2. The fact that Houston rated over Dallas is stupid. Even if you separate Dallas from its metro area (which is foolish) there’s just a lot here. Throw in the surrounding metro without getting into Fort Worth and there’s a ton. Bring in all of DFW and you have everything.

    I drive rideshare and I tell my out of towners: the WHOLE WORLD is in Dallas and they bring the best with them, so you can get ANYTHING here. And it’s true. Pick a food, a music, an art, it’s all here, almost every night, safe and cheap. Everyone just wants to live in peace and prosper. I drive in a suburban area that’s America’s corporate HQ. Seriously. They’re all there, so the area is blanketed in shops, dining, and entertainment for all those employees and clients brought in for meetings and conventions. Four huge complexes full of restaurants and bars as well as shops and entertainment options, and that’s just 3 square miles well north of Dallas. Just one spot!

    Yeah, I’m calling shenanigans on this. Houston? What great fun do they have again? Flooding every time it rains more than an inch because they built a city in a giant natural bathtub?

  3. For the list of boring places, I would suggest Little Chicago, Minnesota. This is not to be confused with Little Chicago, Wisconsin. That Little Chicago may be more famous than the Minnesota one, but only because it is not possible for it to be less famous.

    I don’t know which one Frank Sinatra may have sung a song about, because I am not that familiar with his work. I aplogize for the omission.

    1. “What do you do for fun?”
      “Not much…mostly toddlin’.”
      “Really? Have I got the place for you!”

  4. Maybe if Laredo could get rid of all those dying cowboys on the streets, they would move further up the list.

  5. North Burlington, Vermont however, watch out. How anyone can pass thru that town without getting arrested is beyond me.

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