Why did Bob Dylan skip Woodstock Festival?

We’ll never again see an event like Woodstock. The 1969 festival was a cultural wonder, a phenomenon that will never be replicated no matter how organisers misguidedly try. Sitting as a kind of finale to the entire decade, the three-day-long festival captured the music, spirit and various subcultures of the last ten years, with some of its biggest stars in tow. One, however, was notably missing. While generations to come look back at the event and wish they could have been there, Bob Dylan didn’t seem to share that feeling as he skipped the event.

While Woodstock is written into common cultural knowledge, its lineup is less well known. To a degree, it feels somewhat unimportant. Even if no one ever got up on stage, the festival would have gone down in history as an era-closing gathering of all the hippies, rockers, Hells Angels and beyond, proving to be one last hurrah for the peace and love generation before the grip of drugs got deadlier and the atmosphere of the times got darker. 

Those on the lineup who have gone down in history as the defining artists of the time were just as much part of the crowd as anyone else. Acts like Janis Joplin, The Who, Santana and Jefferson Airplane graced the stage but stuck around the witness history being made. A six-month pregnant Joan Baez closed out the first day. Grateful Dead extended their track ‘Turn On Your Love Light’ into a 36-minute-long epic. Jimi Hendrix did his infamous dawn rendition of the national anthem as the show rolled on all the way through the night. 

However, one figure that people assume would have been there was Bob Dylan. As a mainstay of the East Coast music scene and a vital force in the 1960s sound, it seems like Dylan should have been at Woodstock, but he sat it out. In fact, he was never really even invited.

Dylan’s absence is made even weirder by the fact that he lived in Woodstock at the time. After settling down with his wife, Sara Lownds, and escaping the chaos of the New York City scene, they moved out to the quiet area. Apparently, he wasn’t too pleased when the festival decided to be held there as he worried it would forever ruin the peace and quiet he’d found and lead people to come knocking at his door. His concerns were clearly loud enough as he was never in any serious negotiations to appear. 

There’s also a more logistical reason for missing the event. He simply had other obligations as he was booked to play the Isle Of Wight festival and was due to set sail on the Queen Elizabeth ship on the 15th of August, the day Woodstock started. His travel plans were messed up after his son became unwell, but that’s beside the point. The point is simply that Dylan wasn’t there because he was expected elsewhere. His band, the aptly named The Band, were at Woodstock, however, before being flown out to Isle Of Wight for Dylan’s headline slot.

The confusion and surprise about Dylan’s absence make sense, though. When you see images of Woodstock with its insane crowds, miles of sprawling, rock-block traffic and hoards of hippies, it seems like everyone in the world must have been there. Or at least, the surrounding myth of the event is that everyone in music was there. It’s held up as the ultimate gathering of all the 1960s greats, where everyone who was remotely artistic at the time scrambled to be there. But that wasn’t the case.

There were actually a lot of rejected invites. The list of artists who turned down the chance to play is far longer than the lineup. The Byrds didn’t see a point in trekking to just another music festival for a relatively small fee. Led Zeppelin’s excuse was the same, feeling like they’d just be another name on a list. Joni Mitchell was too busy, despite later writing a song about the event. Frank Zappa thought it would be too muddy. So many names like Free, The Beatles, The Stones, Simon and Garfunkel all said no to the festival, either prioritising other events or simply not being that fussed.

So, while Dylan might have been the king of the New York folk scene and a literal resident of Woodstock, his lack of interest in attending is only weird with our rose-tinted retrospective view of the event. At the time, a fair few legends ditched the iconic affair, whether they later regretted it or not.

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