I think its important to at least glimpse the context of the Bob Dylan Concert at the 1969 Isle of Wight Festival. It was a terrifically special gig - perhaps especially for us locals in the West Wight, who teamed-up to help the Foulks, who organised all this from their mum's house in Totland.
A small group of us at Carisbrooke Grammar School and Gunville Priory school (including me, Derek Rath, Theresa O'Driscoll, Pauline Bennett, John Humphries, Chris Hann) had almost unconsciously found ourselves getting really interested in the Beatnik books just beginning to appear in second-hand bookshops - these included Kerouac's On The Road and The Subterraneans (1959), Ginsberg's Howl (1956), Burroughs Naked Lunch (1959). We called ourselves Ravers, Beats and Geeks - we went-in for tousled longish hair, second-hand clothes put together (almost choreographed) with a sense of 'underground' style - and folk clubs, jazz clubs and the Blues. And Ray Foulk was part of this scene, fresh from the Bluecoat School in Liverpool - he had been to the Cavern Club - had seen the Beatles!
I had left Carisbrooke and gone to Portsmouth Art School in 1963, by which time the British Blues scene was bopping, and I had hitched to Guildford to see the Rolling Stones and the Eel Pie Island and Richmond Blues fans at close quarters. It was a bit of a revelation - they were people just like us...

And that year - 1963 - had been an especial revelation for me, growing up at 17 years old, going on the 1963 Aldermaston March, seeing John Boorman's television programme Citizen '63, hitching 60 miles up to Guildford to see a Rolling Stones gig, meeting my first Mod girlfriend (aah Monica Burton in her tartan maxi-skirt and skinny blouse) at the Royal York Hotel in Ryde, and going to Portsmouth Art College that September, and soon after seeing that first James Bond movie - with its fabulous Maurice Binder titles:
https://www.youtube.com/watch?v=RFmTv9413tw&t=6s



And that September meeting Pete Harris - who kindly loaned me half-a-dozen really lifelong-important albums (LPs) he had brought back from New York: the Bob Dylan debut album, and LPs by Joan Baez, Carolyn Hester and Huddie Ledbitter (Leadbelly) and Harry Everett Smith's Anthology of American Folk Music - the album that helped kick-start the NY folk revival of the late 1950s and early 1960s.

So thanks Pete Harris, wherever you are now - these LPs brought me instantly up-to-speed with the New York folk scene - the scene that launched protest-songs for a new post-Pete Seeger generation and began the journey to Folk/Rock courtesy of Bob Dylan a few years later.. So 1963 introduced me to politics, underground culture, sex and style - and I got my first scooter - a Lambretta D-Type - for 10 quid - did i think I was cool...

And this was right at the beginning of the Sixties - and we learned a lot quite fast. I had already discovered that I liked Jazz-poetry - thanks to that brilliant EP of Christopher Logue reading Pablo Neruda poems with Tony Kinsey's modern-jazz backing - it was called Red Bird:

And gradually, being a hyper-inquisitive art student - I picked up on Richard Hamilton, John McHale and Eduardo Paolozzi (and the rest of the Independent Group - those guys who invented Pop Art from the late 1940s onwards) and also Ken Russell's short TV documentary set in the Royal College of Art: Pop Goes the Easel. (I once found myself standing behind Ken Russell at Brokenhurst station (in the 2000s) waiting for the London express - he was talking loudly on the phone, giving someone his personal ID and bank-account number...)
https://www.youtube.com/watch?v=7iObj0AfuOI


Richard Hamilton's famous 'Pop' collage: Just What is it that makes Today's Homes so Different, So Appealing? of 1956, and Paolozzi's Bunk! Collages from a decade earlier:

So - I won't relate my adventures over the next several years - if you're interested you can download my Sixties book:

So this was by way of an apropo for the 1969 Dylan IOW Festival it indicates part of the reason we felt so good about having Bob Dylan - this mythical poet/songwriter/icon - on our own Isle of Wight that year...
The build-up after these early years included the absolutely key albums Bringing it All Back Home (1965), Highway 61 Revisited and Blonde on Blonde 1966.