West of Harriman State Park, the Appalachian Trail and US-6 cross the busy I-87 New York Thruway, then wind through the exurbs of the Big Apple, where town after town seems unsure whether this is country living or not.

Farther west, along I-84 on the tristate (New York-New Jersey-Pennsylvania) border, Port Jervis is a curious mixture of small-town dereliction and commercial bustle. Transportation has clearly been a major historical force here, with the influence of successive eras—the river, the railroad, and the highway—inscribed in the very layout of the town. Stop inside the old Erie Hotel and Restaurant (845/858-4100, around $69 and up) next door to the former depot, which has an ornate bar, a lively restaurant, and rooms upstairs.

About 30 miles northwest of Port Jervis, Max Yasgur’s farm outside Bethel, New York, welcomed revelers to the August 1969 Woodstock Festival of Music and Art, starring Jimi Hendrix; Crosby, Stills and Nash; and some 300,000 mud-soaked hippies. Starting with a 30th Anniversary concert in 1999, the Woodstock site has been redeveloped into a community-based arts and performance center called the Bethel Woods Center for the Arts (866/781-2922), which has a 15,000-seat amphitheater and a good museum tracing the story of the Woodstock generation in pop culture and pop music, self-described as a “destination for anyone who lived through the sixties or wishes they did.”