Closest city on East Coast/Midwest to Portland...

[ComfortablyNumb]

Minneapolis does feel sort of northwestern, but not really when you stay there awhile. The people are very mid-western.

I'd say Madison, Wisconsin like the other guy. I lived there for 5 years during college and it is a lot like Portland, although I'd say a little bit more white-collar and quite a bit smaller (Around a 600,000 metro area compared to what, 2,000,000?). Currently they are even building a light-rail that stretches the entire length of the city. The population is very educated and EXTREMELY liberal, and there is a very present drug culture in many neighborhoods and marijuana is legal so you probably won't be charged for possession. Like Portland, it has a serious homeless problem, though. On any given night downtown you'll find people sleeping on the sidewalks, in bus shelters, etc. It also has a pretty visible Portland-esque "slacker/punk class" who often make condescending remarks to the college kids. They pretty much have their own bars, neighborhoods, restaurants, grocery stores, etc. I'm not sure how they pay their rent.

[MovinOutWest]

It doesn't quite have the size of Portland, but for a similar liberal feel try the Northampton/Amherst area of Massachusetts. It's much smaller and has more of a college town feel than a big city feel. But after spending time in both I'd say they are fairly similar when it comes to liberal leanings.

[pretzelman]

Ithaca NY has to be up there, it's like a little version of Portland in many ways.

[JakeDog]

Portland is like a mixture of Pittsburgh and Berkeley. Sure it is liberal, but it definitely has a gritty side to it.

[bigdave01]

I've always heard comparisons of Austin and Portland. I still think Minneapolis would be a good choice.

[Wherewillitland]

haha Portland, Maine is surprisingly similar to Portland, Oregon.

Ashville, North Carolina

Syracuse, New York

New Paltz, New York.

All of these places are much smaller but still have an urban feel.

[pretzelman]

Originally Posted by JakeDog

Portland is like a mixture of Pittsburgh and Berkeley. Sure it is liberal, but it definitely has a gritty side to it.

I did not find anything gritty about Portland when I lived there, but I grew up in Philly, so it's all relative I guess. Otherwise your analysis makes sense though. Portland did remind me of Pittsburgh in that it's of similar size, has a lot of bridges, and is generally friendly and laid-back.

[nanannie]

Asheville NC--fer sure

[PDXmom]

Originally Posted by The Cactus Leaguer

Liberals in other parts of the country are different than the West Coast, so there is really no comparison. In terms of "look and feel", I think that the two most similar cities to Portland are Cincinnati and Pittsburgh (just replace the sports stadiums with light rail and bike paths ). But in terms of politics, your best bet is to check out the larger university towns. I like the suggestions of Madison, Ann Arbor, and Raleigh/Durham... I'd put Austin in that category as well.

Summer 07 I moved from Portland (lived there 20 years) to Durham, NC. And there is no where in this state like Portland. Asheville has a bit of a funky, liberal, outdoor vibe to it. But it is tiny!! And the second you leave Asheville there is a huge difference. Durham is not like Portland. Durham feels more like a small town than a city. And while it's liberal for the state it's not the same magnitude. Raleigh is even less like Portland. Chapel Hill thinks it's the liberal city of the SE, but as someone else eloquantly put it.... liberal on the west coast is 60s hippies but in towns like CH it's tweedy college professors.

If you've never actually lived in Portland, you might not see these differences. If you try one of these places in Durham stick to the areas near Duke, in Raleigh you will want to be Inside The Beltline (ITB) and Asheville you'll not want to be outside of Asheville.

Also there is no comparison to the mass transportation, walkability and bike friendliness of Portland. YOu will not finda a similar level or scale in this whole state.

[chitown3pa]

Originally Posted by healinghands

What would be the most similar city in the Southeast US or Midwest to Portland? I am looking for that liberal feel just not able to move to West Coast at this time. Thanks.

Madison, WI