Bob Dylan & The Birth of Woodstock’s Music Scene

“‘There must be some way out of here,’

said the Joker to the Thief.

‘There’s too much confusion;

I can’t get no relief.’”

-Bob Dylan, “All Along the Watchtower”

Bob Dylan’s tie to Woodstock, New York, is etched in the mythos of American music. In the mid-1960s, he drifted north to the Catskills, drawn to the town not for its fame but for its quiet remove, a place to disappear after the crash of his motorcycle in 1966 and just after the freewheeling success of his classic album The Times They Are A’Changing in 1964. What he found here in Woodstock was a rhythm outside the spotlight: backroad solitude, small-town stillness, and the chance to rework his sound.

In a house known as Big Pink, on the outskirts of town in West Saugerties, Dylan joined forces with The Band. Their basement sessions, which he described as half experiment, half exorcism, spooled out into what the world later called The Basement Tapes in 1975. The songs, raw and unpolished, pulled away from the electric roar of his mid-60s sound and toward something older, earthier, closer to the grain of folk and country, just like Woodstock itself. In that retreat, Dylan sketched the beginnings of what came to be known in the music world as “Americana.”

Though he never stepped onto the stage at the 1969 Woodstock Festival, his shadow hung over it. Promoters borrowed the town’s name precisely because Dylan had made it a kind of sanctuary. Woodstock became shorthand for a cultural shift, a gathering point of art, music, and myth, and Dylan’s guiding presence was the beacon, even in absence.

About Dylan’s Studio

This expansive suite spans the entire first floor of The Main House. It’s a bright and soulful space that features modern design, rows of windows on two sides that invite that inspiring mountain cross breeze and a wall of windows in the back that face our grounds, the brook, and the fields of the historic Comeau Property.

The suite is accessed through a side gate from Tinker Street that leads to a private bluestone patio and entrance in the back of the house. In the front half of the space is a large living area, a reading area, and an alcove sleeping area with a Queen-sized bed. The modern, velvet sofa opens up into a extra large twin, and comfortably accommodates an adult. Head further back into the unit to a large, well-stocked and brand-new kitchen with a dishwasher, microwave, breakfast bar, and a step-down breakfast nook with great views of the rolling green yard. The recently-renovated bathroom features a glass-enclosed shower. This suite is perfectly suited for 2-3 people and great for those traveling with dogs.