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Places 📍 Brattleboro, Vermont and other very crunchy towns: what's their future after the hippies age out?


Dear Leader
Staff member
I recently became curious about Brattleboro, Vermont, because it shares a lot of traits with the Upstate New York community where I now live. When I visited Brattleboro during a recent road trip through New England, I thought "this all looks really familiar." Brattleboro, like my neck of the woods, was something of a hippie, lesbian, and back-to-the-lander mecca in the 1960s and 1970s. This gave the town a "crunchy" reputation, which drew in a hippie adjacent crowd -- artists, folk musicians, writers, craftspeople, and the like -- who can work from anywhere, live simply, or live off a trust fund or the pocket change of wealthy parents.

Brattleboro is geographically isolated (although next to an Interstate highway), and not within commuting distance of any place besides ... oh, Keene, New Hampshire? It has a thriving downtown, with no urban renewal-era scars that I could easily see. Neighborhoods surrounding downtown have the same kind of aging frame housing stock and intentionally unkempt look that's so common back home.

Unlike the town where I live, Brattleboro has no employers, industries, colleges or universities, or tourism attractions of note. Windham County only has a population of 43,000 residents, of which 12,000 live in Brattleboro proper. Median family income for Windham County is on the low side (US$46,989), and 6.1% of families live under the poverty line. (Median family income in the county where I live is US$90,192, despite a landscape of crushing Appalachian-style poverty in some areas.) Housing costs are high relative to income, but overall a bit lower than the area where I live. Brattleboro's size also means it really doesn't have much name recognition outside of New England. It also doesn't have much of a critical mass to support economic growth from within, or institutions meeting the cultural or religious needs of ethnic or religious minorities.

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Windham County is very white by American standards, but it's not like Reykjavik, Torshavn, or a bonspiel at the Bemidji Curling Club. I saw enough black and Hispanic people in Brattleboro to make me reassess the "Vermont is lily white" stereotype, at least for Windham County. On the surface at least, Brattleboro doesn't appear to be a kind of place that's hostile to people of color or non-European immigrants. Whether people who aren't of European descent feel like they're truly a part of the larger community, though, I can't say.

One thing that really struck me about Brattleboro was the sight of so many old people. I'm not talking Florida retiree types, but rather graybeard and graymane Boomers; liberal arts professor-looking men and British garden lady-looking women -- again, kind of like here at home. However, unlike home, I saw relatively few young people in Brattleboro. I feel conspicuously old whenever I visit NYC, Washington, or Toronto, and see relatively few people that look over 45 t0 50 out in public. In Brattleboro, it was the opposite. I felt like if I lived there, I'd have a lonely existence at the bottom of a deep demographic hollow; a ravine between the under-30s working in the coffee shops and restaurants, and the Boomers that, on the surface, seem to made up the rest of the population.

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The influx of hippies likely kept Windham County's population growing after the region de-industrialized. With younger generations being more about back to the city than back to the land, though, I wonder what's going to happen to places like Brattleboro after its Boomers age out. Did the hippies save Brattleboro from the fate of economic decline, or just give it a reprieve? Are there enough Generation Xers, Millennials, and Zoomers who idealize small town living or rural life, and can carve out their own niche to make a living, to replace the Boomers? Can "crunchiness" alone sustain an isolated small town in the long term?


Here's their Town Plan- actually better on the employment front that I thought they'd be (it's not all retail/tourism- page 18) but they acknowledge aging housing stock and lots of people living in out-of-town rural sprawl subdivisions and commuting into town for work. Medical is big so the hospital's a driver for sure.