Because it lent its name to the 1969 Woodstock Music Festival—which was actually held in Bethel, in the southwestern region of the Catskills—this town has inadvertently been called upon to define an entire generation. It's an amber-tinted vision of the past, where the counterculture lives on through the occasional tie-dyed T-shirt or banner emblazoned with a peace sign.

Woodstock's main street hugs the small town green, where artists, musicians, political protesters, and the occasional pet parade convene. Although eclectic boutiques, bookshops, 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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