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For me?
Milwaukee, WI
Baltimore, MD
San Antonio, TX
I'm curious as to why you think Portland is underrated? It's constantly in Forbes lists for being one of the "10 best" of whatever the list is on and it's a major destination for tourists (in fact, tourism is its biggest industry). I have a hard time thinking of a city of around 65,000 people that gets nearly as much attention as Portland. Maybe Asheville NC, but not many others. Obviously I don't think it's underrated (I lived there for four years and was very underwhelmed), but I'm curious as to why you think it is?
I am referring mostly to this site, and I love Portland, ME it's so beautiful of a small town.
Of the cities I've visited(I'll exclude Milwaukee, since I think enough people recognize how good of a city MKE is):
1) Pittsburgh
2) Saint Louis
3) Indianapolis
Honorable mentions to Louisville, KY, Cincinnati, OH, Cleveland, OH, Detroit, MI, Nashville, TN, Tallahassee, FL, and Greensboro, NC.
I excluded cities I haven't visited from the list. Still a notable number of cities I've yet to visit, and I don't have time to list all of them in this post.
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