What are your favorite small(ish) towns? 

Say ~10K-200K pop in any country, places that punch well above their weight 

A couple of mine:

San Sebastián, Spain 
Tofino, British Columbia

Where else?

Crested Butte, CO
Jackson, WY
Telluride, CO
Whitefish, MT

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yes, though these places (especially jackson) are just as good (maybe better?) in summer

never been to whitefish in winter

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totally forgot about telluride, such an amazing place