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.
Pierre, South Dakota. I’m actually from Iowa (I live in Los Angeles now) and my family went on vacation to South Dakota one time. I remember driving to the capital and realizing it was smaller than my hometown in Iowa!
I get that feeling you’re talking about with Des Moines. I used to go on tons of long road trips around the Midwest around age 18, looking for something new. Coming back to visit, Des Moines always feels comically small — I find myself wondering how businesses stay in business with such few customers.