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Both are very underrated downtowns, but I'd have to go with Portland.
It's a truly walkable, compact, fun downtown with several unique districts that have a lot to offer. It feels like you can get anywhere in 5 minutes when youre in Portland, and yet its dense with restaurants, retail, bars, etc...Although its much smaller than, say, NYC and SF, it is one of the best DTs in the country for urban accessibility.
I'm gonna pull a homer on this one...Milwaukee City. For the reason's of nightlife and restaurants although some include The Third Ward into downtown Milwaukee b/c it's like the gas lamp district of Milwaukee. You can't tell the difference between downtown Milwaukee and the Third Ward it runs right into it. I have never been to Portland but from pics and second hand stories it sounds a bit to granola for me.
Portland's downtown is more happening and better served by public transport and thus has a better downtown. But I cannot emphasize enough how underrated Milwaukee's downtown is given its historical architecture, riverfront, and stunning lakefront setting.
BTW Milwaukee City,
Great pics, but please refrain from posting images depicting douchebaggery and Paris Hilton when boasting about Milwaukee. Not only is it a total misrepresentation as the city is known for its laid back bars, but it also will attract ridicule and vitriol by our C-D brethren.
Yep. I wouldn't brag about Paris Hilton being in town. I love Milwaukee's lakefront but the downtown area is kind of (dare I say) boring. I would go with Portland on this one. Speaking of which, I was surprised to see so many empty places in the Grand Avenue Mall last summer.
I've always had a blast going to Milwaukee from Chicago. They have an awesome downtown. I think it really gets overlooked because it's so close to Chicago, and also that it lies north of Chicago. You almost have to pass through Chicago to get to it from anywhere except the Twin Cities.
It's still a decent size city though, 1.7 million in the area, and Chicago has almost 10 million, and burbs from each city are finally starting to run into each other.
all from flickr
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