I’ve been doing a little research on songwriter Bob Dylan. Like most riders, I already knew about his mysterious wreck near Woodstock, New York, in 1966, where he dumped his Triumph, injured himself to an unknown degree, and went into seclusion for a while.
However, in reading through books about Dylan, interviews with people who knew him prior to his arrival in Greenwich Village, and his own Chronicles: Volume One (2004) I turned up a few references to Harleys, time spent running with the biker boys in his hometown, even being a bit of a “rough, tough” character. I don’t know how true any of that is, but he apparently did spend some time around riders, as seen in the photos below.
1956, with a friend’s Harley-Davidson FL:
1966, on the Triumph he later wrecked:
I always cringe at this one, because for some reason he’s dangling his feet – not a smart thing to do and goofy-lookin’ to boot!
The passenger below is identified as John Sebastian of The Lovin’ Spoonful, who went on to have a solo career as a folkie in the early ’70s. He was one of five acts on the bill at the very first real concert I ever attended*, at Randall’s Island, New York City, on July 17th, 1970. The others were Jethro Tull, Steppenwolf, Grand Funk Railroad and some guy named Jimi…. Jimi Henderson, or Hendricks, or some such. I wonder whatever became of that fellow? 🤷🏻♀️
I’m not sure of the year – probably mid-’60s – but Dylan appears to be riding a Yamaha….
….and in 2004, back on a Harley-Davidson!
One more, of the man on an entirely different kind of bike….
.…but wearing a motorcycle club jacket. Go figure!
UPDATE: 28 SEPTEMBER 2023
When I first published this article a little over ten years ago, I included the photo seen below. The image appeared in a book about Harleys, and although the rider was unnamed, the text placed the rider in the vicinity of Dylan’s hometown of Hibbing, Minnesota. Between that and the rider’s resemblance to a young Bob Dylan (and some wishful thinking and exuberance on my part) I initially felt safe in making the leap. However, my journalistic integrity niggled at me — I couldn’t swear that the knucklehead rider was, in fact, Bob Dylan — so I removed the photo.
Later, a post at Revzilla confirmed my original suspicion, so I am reposting the knucklehead photo.
….but wait! There’s more!
It has since come to light that Bob’s father, Abram Zimmerman, was also a rider. The photo below shows a young Mr. Zimmerman in 1938, aboard a Harley-Davidson flathead. The ‘F.C.’ carved on the battery box is for the Flying Cuyunas Motorcycle Club, founded by Duluth-based miners from the now-inactive Cuyuna Range. The pennant on the handlebars is apparently from the Beaver Bay MC, a friendly club the FCMC shared rides with.
Funny thing but, like Bob’s father, Abram, my father rode motorcycles prior to beginning his family. Unfortunately, and unlike Abram, my father was not about to buy his kids motorcycles. He never even told us that he once rode, despite the fact that my brothers and I all had two-wheeled fever to some extent. Hell, we weren’t even allowed to have mopeds or minibikes!. 🙄
It wasn’t until I became an adult and had owned my first Harley for several years that I learned about my father’s history with motorcycles: that he won the money for his Indian Chief in a poker game 😎, that he rode after the war 🤠, that he had a get-off serious enough to convince him motorcycles were not the best choice for a family man 😮, and that — most importantly — he never got over his love of the damn things! 🤷🏻♀️ He never told us about his motorcycling exploits when we were kids because he didn’t want to risk encouraging us to do something he knew to be dangerous 🤔, but once I had my own bike it was something we could share; something we bonded over in the final years of his life. In fact, I am always patient with the oldtimers who approach me to say, ‘I used to have one of those….’ in part because my father was one of those guys! 😁
* The New York Pop Festival was actually an ambitious effort to recreate the three days of Woodstock (held the previous August) within the city limits. It turned out to be overly ambitious, but the first night — the one I attended — was freakin’ awesome!!! 🤘🏽 Look at that line-up!
I have written an essay about the New York Pop Festival — the production history, my experiences and the impact it had on my life — and will use that to create a separate post about the concert ASAP. For now, though, just look at that price: $8.50 to see five of the biggest names in rock music! 😮
The Shovel Shop 
Pretty Cool
The unknown passenger is
John Sebastian
Photograph by
Douglas T Gilbert
More pictures of him and Bob in the book
Forever Young