Iconic troubadour Bob Dylan brought his timeless sound to the historic coastal town of Plymouth, launching a creative caravan that would entertain and surprise audiences with almost no warning.

At the end of October, 1975, Bob Dylan and the Rolling Thunder Revue descended upon Plymouth, MA, to kick off one of the most beloved tours in rock history. It was a big year for massive bands at a pinnacle of the genre’s influence—acts such as the Rolling Stones, Led Zeppelin, Black Sabbath, and Parliament-Funkadelic had torn through North America during the spring and the summer—but Dylan’s tour stands apart. In 2019, Martin Scorsese released The Rolling Thunder Review: A Bob Dylan Story, a documentary-cum-concert film on Netflix that chronicles the whole messy experiment. Ironically, when asked what remains of the tour today, Dylan replies, “Not one single thing. Ashes.” Perhaps this is true in a metaphysical sense, but plenty of relics have endured. The Bootleg Series Vol. 5 came out in 2002 to critical acclaim featuring selections from various stops on the journey, and in 2019, a 14-CD box set of 148 tracks was released to accompany Scorsese’s film. On YouTube, one can even find poor-quality mono recordings of the first night at Plymouth Memorial Hall. Of course, these spectacular nights endure in the minds of audience members and Dylan’s fellow troubadours such as singer Joan Baez and actress Sharon Stone. As a performer and sometimes reluctant influencer of culture, the 2016 Nobel laureate frequently reinvented himself or created something new out of old work, often writing or singing new lyrics to his songs, constantly updating and revising. In Scorsese’s film, Ruben Carter—the falsely convicted boxer about whom Dylan wrote “Hurricane,” which debuted on this tour—recalls asking the songwriter what he was searching for. He recounts, “Bob would say, ‘I’m...