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The only problem with Seattle and Denver - higher costs of living than many of the other cities.
Asheville and Boise are both good in the sense that they're moderate in size...yet they have enough going on. They also have the right weather conditions, and they're relatively inexpensive. You'd get more for your money.
Northampton MA near the Berkshires is extremely liberal. A little on the expensive side , but doable. Not like Colorado ($$$). The scenery is beautiful, there is lots to do (not a ton but enough), cafes, theater, Umass amherst, public transportation, great proximity to other locations. There is also North Adams MA, but that is a wayyyy small city, although it has Mass MOCA, two colleges nearby, righ at the foot of Mt. Greylock (tallest point in MA), very close to State Parks...in fact you can walk to one. Right next to the border of vermont and green mountains. Maybe not enough young people for you there besides college students (so it has a very transient vibe) because there is not a lot fo employment there.
Portland, ME is a great place to live. I do recommend visiting first however. If you travel north you will find very small country towns. Some are overwhelmed by this. The Old Port is a really fun downtown, lots of young people. Maine is a fantastic state, the people are very friendly and the area is very dog friendly. I will say however that Downtown Portland, ME is an expensive place to live. A couple of years ago I read an article that said Portland housing was equal to housing in Boston, MA. Seems silly because Boston is Boston and Portland, well, isn't. I recommend Maine to anyone.
North East cities I would consider:
Providence, RI
Portsmouth, NH
Portland, ME
Burlington, VT
In other words... anywhere in northern New England.... with Providence thrown in for fun.
Maine is incredible.
JoshB:
Quote:
Madison, WI
I've heard it is good to. Looks on the map like it's sandwiched between two lakes. Might be making a trip up that way this summer.
Denver isn't *that* expensive. Less expensive that Seattle, I believe. My DD has a 2 BR apt in a nice, safe, city neighborhood for $650/mo. Boulder is an extension of Denver.
Denver is less expensive than Seattle by a fairly good margin. A bit overpriced in the city itself, but you're right, there are a lot of affordable towns nearby.
Madison is great, but you're not going to find the caliber of outdoor activities you can find out west - Portland, Seattle or Denver.
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... with Providence thrown in for fun. 
