My pick is Des Moines, currently living here. Like, there’s almost nothing worthwhile to see and there are pathetically few skyscrapers. I live in an area where I can get a good picture view of all of the buildings within sight.
And all I can feel is “…there should be more”. The buildings themselves aren’t even that interesting. Des Moines tries to make itself feel big and comparative to other cities, but it just cannot do that.
My other pick is Montpelier in VT, where I have also lived. Everything feels too damn clustered. the neighborhoods are on steep ass hills with awkward traffic markings. There’s almost zero reason to really do anything there and it can easily be missed. Like, you can drive from Barre and through Montpelier before you know you’re on the highway out of Montpelier.
Hey I used to live in Des Moines! I agree with you. Iowans treat Des Moines like a city. “I have to go into the city today”. No you don’t. You have to go into town. Des Moines is a big town, it’s not a city.
They refuse to believe they’re a city, any time they’re faced with acknowledging they might be becoming a city they do something regressive to it to try to prevent it. Built out not up. Kill all mass transit ideas. Anything diverse happening? Let’s keep that in check. They are a city of 300k that want to run it like a small town. Then the politics, just yuck the people who run it.
There were some fun places, the east side had some good bars, the keg stand in WDM was my stomping ground for a while, but so many people are just happy to have their strip malls and chain restaurants. Oh my god we got a Texas Roadhouse, I remember it made the news when Des Moines got one. God forbid anyone try an actual good local place.
Depending what you want to dive into I can definitely tell you more good and bad