An arts colony and a haven for eccentricity, Woodstock is the almost mythical wellspring of alternative American culture and home to many of the now deified promulgators of the seemingly endless phenomenon of the 1960s. In having its name usurped for a seminal music festival in 1969 (actually held in Bethel, in the southwestern region of the Catskills), Woodstock has inadvertently been called upon to define an entire generation—or at least the amber-tinted soul of its lost youth.

Woodstock's main street hugs the small town green, where angst-ridden teenagers, musicians, political protesters, and the occasional pet parade convene. Although eclectic shops and art galleries help maintain the town's status as a countercultural magnet, the current scene is rather mellow. These days you're more likely to spot Land Rovers than VW buses in town, where aging hippies and baby boomers, families, and celebrities share sidewalks with out-of-towners. To enjoy Woodstock's charm, don't overlook the details—the gently gurgling brooks, the odd homegrown bench, the twinkling lights that come on at dusk—and consider visiting in winter or spring, when crowds thin out and traffic eases.

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