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Here's a fun one for people who like rankings and lists.
Brattleboro comes in #2 in the list of Top Ten Charming Small Towns In The US, according to the tripadvisor.com, a site that is not really that charming but rather database-generated and non-human.
Nonetheless, we're number 2! Take that, Mendocino and Bigfork.

screenshot of top 10
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Flagstaff is OK. The best thing about it is that it is situated in a place that is convenient to other great places, for instance, Grand Canyon, Monument Valley, Sedona, etc. Its quite a lot larger than Bratt though.
Rockport is a different kind of charm all together. Definitely MAINE and oriented toward the harbor.
I'll have to check out Ashland, Ore when I'm out there in late August.
Personally, I think Burlington is pretty much the most charming and happening place I've visited in the east, for a small town. Asheville NC is a really hip place too. Lots of charm, lot of variety. Very cool.