
Bob Dylan’s songs have seeped into the public consciousness during his remarkable career, which spans more than six decades and encompasses an extraordinary number of different musical styles and genres. But Dylan also expresses his creativity in other ways, and in the last two decades, he’s become a respected and much sought-after visual artist as well.
Dylan’s artwork is most popular in the United Kingdom, and prints dominate his market, accounting for a massive 99% of all his work sold at auction, with most prints reaching between £1,000 and £5,000. Many of Dylan’s most popular prints are those from his Side Tracks series; based on his iconic Train Tracks sketch (which first appeared in his Drawn Blank series), the image is often considered Dylan’s most popular and widely sought-after.
As a result, Side Tracks is a running series currently numbering more than 300 giclée prints, each of which begins with the same Train Tracks image, but is then hand-embellished by Dylan, making every one unique. All the prints are individually named after a specific location and date, which usually corresponds to a concert Dylan played at some point between 1961 and 2013.
Part of the Side Tracks prints’ appeal is the way they encapsulate the restless romanticism of the sense of constant wandering that imbue so many Dylan songs, as well as his public persona. Trains have also appeared in countless Dylan lyrics, often representing change, moving on, and reinvention, and frequently tying into American train folklore.
Bob Dylan’s Side Tracks prints are so popular, this article is dedicated specifically to them; to find out more about Dylan’s other most expensive prints, read this article. Alternatively, read on to discover Bob Dylan’s six most expensive Side Tracks prints. If you own one of Bob Dylan’s Side Tracks prints and want to know more about how much it might be worth, or how to sell it, get in touch with Mark Littler today.
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18 May 1976, Oklahoma City, Oklahoma
This giclée print was sold by Roseberys in July 2022 for £32,000, exceeding its top estimate by £10,000. It’s named after a concert Dylan played at the State Fair Arena in Oklahoma City on Tuesday 18th May 1976, just one week before the end of the famous Rolling Thunder Revue tour.
Already a world-famous musician, the aim of the Rolling Thunder Revue was for Dylan to play smaller, more intimate venues, as opposed to the huge, big-budget tours that had become expected for musicians with his level of popularity. Several other performers, musicians, and friends came along, too, and Dylan and his entourage took to wearing face paint, masks, and flowers in their hats, giving the entire thing a surreal, carnivalesque feel to it. This seems fitting, since when he first arrived in New York, Dylan (who always loves to weave fact and fiction to reinvent himself) claimed that he’d spent his teenage years as a runaway living in a circus, expunging the truth of his middle-class Minnesotan childhood.

3 February 1991, Glasgow, Scotland
On 3rd February 1991, Dylan played at the Scottish Exhibition and Conference Centre in Glasgow; this print, named after that concert, was sold by Roseberys in November 2023 for £32,000. Already several years into his popularly-named Never Ending Tour, Dylan played some of his best-known songs in Glasgow, including ‘Mr. Tambourine Man’ and ‘All Along The Watchtower’, the lyrics of both of which were featured in his Mondo Scripto print series.

7 June 1989, Birmingham, England
Named after a concert Dylan played at Birmingham’s NEC Arena in 1989, this print was sold by Forum Auction in October 2024 for £22,000. Dylan’s mastery of colour is excellently displayed in his Side Tracks prints, including in the vibrant orange sky of this one. All of the prints from the series have a slightly different feeling to them thanks to Dylan’s hand-embellishments; when describing his use of colour, Dylan wrote that “every picture spoke a different language to me as the various colours were applied.”

4 May 2002, Brighton, England
At this concert performed at the Brighton Centre, Dylan, as he often does, played a mixture of newer and older songs, and, as always, took great pleasure in reinventing classics that the audience knew well. Sometimes, Dylan experiments with well-known songs so much in performances that the album versions are hardly recognisable, but his audiences have come to expect and love this; it’s what keeps him interesting and exciting after all these decades on stage. In many ways, the Side Tracks prints are created in a similar way, since they are all variations on one image. This print, named after the Brighton concert, was sold by Rosebery’s in November 2024 for £20,000, demonstrating how in-demand the series is.

14 October 1987, London, England
Bob Dylan’s Temple in Flames Tour began on 5 September 1987 and culminated in four concerts in London’s Wembley Arena between the 14th and 17th October the same year. The tour also featured Roger McGuinn (who had been the frontman of the Byrds) and Tom Petty and the Heartbreakers, and the 14 October concert opened with one of Dylan’s most famous songs: ‘Like a Rolling Stone’. This print named after the concert was sold by Roseberys in November 2024 for £20,000.

9 February 1991, London, England
So much of Bob Dylan’s work features themes of travelling and moving on, so it’s no surprise that the man Joan Baez once called “the original vagabond” is obsessed with trains as a motif; as he once wrote, “I’d seen and heard trains from my earliest days… The sound of trains off in the distance more or less made me feel at home.”
Trains even make an appearance in some of the songs Dylan played at London’s Hammersmith Odeon in February 1991, including ‘Stuck Inside of Mobile with the Memphis Blues Again’ and ‘Bob Dylan’s Dream’. This print named after the London concert was sold by Rosebery’s in September 2024 for £20,000.
