Currently embarked on a 10-day road trip through Asheville, Black Mountain, and Greensboro, North Carolina, then on the Lexington, Kentucky, and Cincinnati.
This was my first time walking around Asheville, and I'm smitten, which led me to think about what makes a good, funky town. My personal roster of such places would include Arcata and Santa Cruz in California; Missoula, Montana; Telluride, Colorado; Athens, Ohio; Rockport, Maine; and, now, Asheville. Probably a few more that aren't coming to mind as I write this. (There are good funky cities, too, including Baltimore and Pittsburgh, but that's for another day.)
What are the essential elements? A yeasty mix of solid local business people, artists and artisans and musicians, good cooks and bartenders, residents who have lived there for at least three generations and residents who have lived there for four or five months, residents in their 40s, 50s, and 60s who have an investment in the status quo and residents in their 20s and 30s who poke them out of smugness and complacency. A local college helps a lot. There needs to be openness to the human cornucopia of sexual, ethnic, religious, and political orientation.
I'm drawn to places with jumbled topography, a layout of streets that could never be described as a grid, alleys, apartments above storefronts, and smart zoning that mandates mixed use.
Coffee shops, got to have coffee shops, with good wifi. And book stores, at least one, preferably three, run and staffed by serious readers.
I look for some sense of history and acknowledgement that it matters. There should be plenty of plaques and historical markers (No. 17 among the Rules of Life: Always read the plaque.) and preserved old buildings and repurposed industrial buildings. I like lots of late 19th- and early 20th century structures; they typically have a lot of nice architectural flourishes. I'm a sign painter's son, so some ghost walls are a bonus.
There needs to be a certain level of prosperity, and this part can be problematic. A shabby, down-on-its-luck town isn't funky, it's just shabby and depressing and full of the bad vapors of resentment. Towns that go too far the other way—all the food and liquor and merchandise pretentiously artisanal and precious and available only to those with robust net worths, those aren't towns, really, they're dispersed, open-air shopping centers for the well off, Short Hills Mall without the roof and canned music. The problem with the essential prosperity is, these days, it's never shared equitably. Towns that rely on tourism are full of those who do the hard work of serving visitors but can't afford to live in town because people like me have moved there and raised the price of housing. All those essential artists and craftsman? Too many of them are working their arts and crafts around being baristas, waiters, and bartenders.
I think the one fundamental element is a population that's mixed in every way, invested in community, playing a long game, and tolerant of constant friction that can be irritating but signals where some civil lubricant needs to be applied and some social settings recalibrated. It's never easy, but the rewards are substantial.