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I think this is where Tourist Towns are the answer.
So:
Mineral Point, Wisconsin
Lanesboro, Minnesota
Galena, Illinois
Grand Marais, Minnesota
Ely, Minnesota
McGregor, Iowa
Eureka Springs, Arkansas
Cooperstown, New York
Portsmouth, New Hampshire immediately comes to mind. Small, urban (downtown, anyway), very artsy and vibrant year-round.
While Newport, Rhode Island has a college, it certainly doesn't feel like a college town and is certainly artsy. It's most lively in the summer (part of the reason it doesn't feel like a college town), but is very active year-round.
I'd put Provincetown, MA in that category too. P-Town is mostly active in the summer and pretty quiet in the winter, but it has a very high number of bars, restaurants, galleries, exhibits, etc. for such a small town.
Although Asheville is above your limit (around 83,000 people), since it's in the south, it has a lot of suburban and rural land within city limits. I think the core of the city feels very similar to a smaller northeastern city.
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