Isle of Wight Festival
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40 free Isle of Wight Festival trivia questions with answers — music quiz, new questions added Oct 2026.
For three summers at the end of the 1960s, a small island off England's south coast drew some of the biggest crowds rock music had ever seen. The Isle of Wight Festival became Britain's answer to the great American counterculture events, then vanished for more than thirty years before returning as one of the country's best-loved summer weekends. This quiz covers both lives of the festival: the legendary early line-ups, the comebacks and farewells, the chaos at the fences and the law that followed, and the headliners, stunts and surprises of the modern event. It is pitched at music fans and festival-goers of every vintage. The opening questions are friendly, and the later ones reward anyone who knows their promoters, filmmakers and hillsides.
30 of 40 questions with answers and explanations. Play the quiz
Q 01Which singer skipped Woodstock, near his own home, to headline the 1969 Isle of Wight Festival?
Bob Dylan
Bob Dylan ended three years of near-seclusion with a set backed by the Band, his first paid concert since a motorcycle accident in 1966.
Q 02Which guitarist played the 1970 Isle of Wight Festival just three weeks before his death?
Jimi Hendrix
Jimi Hendrix took the stage in the early hours of 31 August 1970 for what proved to be his last full concert in Britain.
Q 03Whose headline set at the 2004 Isle of Wight Festival proved to be his last full concert in the UK?
David Bowie
David Bowie had an emergency angioplasty in Hamburg twelve days later and went on to retire from touring.
Q 04Which band's 2007 Isle of Wight Festival set was their first British festival show in over thirty years?
The Rolling Stones
The Rolling Stones had not played a British festival since Knebworth in 1976, and the 2007 event sold out in under five days.
Q 05After the 1970 Isle of Wight Festival, what did Parliament restrict on the island without a licence?
Large overnight gatherings
Large overnight gatherings of more than 5,000 people needed a special licence under the Isle of Wight County Council Act 1971, and no festival returned until 2002.
Q 06Which band played the 1969 and 1970 Isle of Wight Festivals, then returned to headline in 2004 and 2016?
The Who
The Who played their rock opera Tommy at both early festivals, and the 1970 performance was later released as a live album.
Q 07Which singer-songwriter halted her 1970 Isle of Wight Festival set to ask a booing crowd for some respect?
Joni Mitchell
Joni Mitchell had been interrupted by a man called Yogi Joe, who took the stage to make a speech; she calmed the crowd and came back for an encore.
Q 08Which band played the 1970 Isle of Wight Festival in near darkness because their singer refused film lights?
The Doors
The Doors performed in gloom because Jim Morrison would not have movie spotlights on the band; the full set was not released on film until 2018.
Q 09Which rapper headlined the 2010 Isle of Wight Festival two nights before Paul McCartney closed it?
Jay-Z
Jay-Z topped a Friday bill that also featured Florence and the Machine and Calvin Harris.
Q 10Which American Idol runner-up fronted Queen when they headlined the 2016 Isle of Wight Festival?
Adam Lambert
Adam Lambert finished second on the show's eighth season in 2009, and Queen + Adam Lambert closed the festival's Sunday night.
Q 11Which county town has hosted the Isle of Wight Festival since the event was revived in 2002?
Newport
Newport's festival site has spread north along the fields of the Medina valley as crowds grew from about 8,000 to more than 50,000.
Q 12Which strait separates the Isle of Wight Festival's island home from the Hampshire mainland?
The Solent
The Solent made 1970 a logistical headache: a crowd far bigger than the island's own population all had to be ferried across.
Q 13Which military display team flew over the Isle of Wight Festival crowd on Saturday afternoon in 2007?
Red Arrows
Red Arrows jets trailed smoke over the site, some fans joked the display beat a few of the bands, and the team came back in 2009.
Q 21Which 2006 Isle of Wight Festival headliner covered Lou Reed's Perfect Day after Reed left it out of his set?
Coldplay
Coldplay stepped in because Reed had left the song out of his own unpredictable set; Chris Martin said Reed asked them to play it to placate the crowd.
Q 22Which headliner closed his 2009 Isle of Wight Festival set by tearing apart his electric guitar?
Neil Young
Neil Young's finale, in a set that also included the Beatles' A Day in the Life, was hailed by the island's newspaper as channelling the spirit of the 1970 festival.
Q 23Gilberto Gil and Caetano Veloso played the 1970 Isle of Wight Festival while exiled from which country?
Brazil
Q 14Which mobile phone maker sponsored the Isle of Wight Festival for three years from 2004?
Nokia
Nokia's deal ended after 2006, which made 2007 the first festival since 2003 to go ahead without an official sponsor.
Q 15Which jazz trumpeter played to the biggest crowd of his career at the 1970 Isle of Wight Festival?
Miles Davis
Miles Davis faced a rock audience estimated at up to 600,000, and a film of his complete set was released in 2004.
Q 16Which Canadian poet and singer played the 1970 Isle of Wight Festival backed by a band called the Army?
Leonard Cohen
Leonard Cohen was on his first ever tour that year, and a film and album of the set finally came out in 2009.
Q 17Realising it would never turn a profit, what did organisers declare the 1970 Isle of Wight Festival to be?
A free event
A free event was the organisers' late concession, although most of the audience had already paid for tickets in advance.
Q 18Which Beatle wrote Behind That Locked Door to encourage the 1969 Isle of Wight Festival headliner?
George Harrison
George Harrison had joined the headliner's rehearsals at a Bembridge farmhouse, and released the song on All Things Must Pass in 1970.
Q 19Which actress, a Hollywood star's daughter, sat in the VIP enclosure at the 1969 Isle of Wight Festival?
Jane Fonda
Jane Fonda watched from a sealed-off area in front of the stage, in company that included Elton John and Françoise Hardy.
Q 20Tom Petty, Pearl Jam and which act formed the American Trilogy topping the 2012 Isle of Wight Festival?
Bruce Springsteen
Bruce Springsteen and the E Street Band closed a weekend when heavy rain turned the ground into a mudbath and queuing cars backed up to the ferry dock.
Brazil's military rulers had jailed both men, then released them on condition they leave the country, so the two Tropicália stars were living in London.
Q 24Which future glam rock star played the first Isle of Wight Festival in 1968 with his duo Tyrannosaurus Rex?
Marc Bolan
Marc Bolan was then playing acoustic psychedelic folk; in 1970 he turned to electric rock and shortened the band's name to T. Rex.
Q 25Which country songwriter was booed off at the 1970 Isle of Wight Festival when fans could not hear him?
Kris Kristofferson
Kris Kristofferson came back for a second set later in the festival, joked that he had brought bodyguards, and was warmly received.
Q 26Which San Francisco band headlined the very first Isle of Wight Festival in 1968?
Jefferson Airplane
Jefferson Airplane topped the bill in a field near Godshill, watched by a crowd of only about 10,000 people.
Q 27Which newly formed supergroup played only their second ever gig at the 1970 Isle of Wight Festival?
Emerson, Lake & Palmer
Emerson, Lake & Palmer built the set around Pictures at an Exhibition, with its Moog synthesizer, and the attention it drew made their name.
Q 28Which Pink Floyd member, at the 1970 Isle of Wight Festival as a fan, was drafted in to help mix the sound?
David Gilmour
David Gilmour had wandered backstage when the anxious sound crew, who were using his band's PA to boost the system, put him to work.
Q 29Which singer pulled out of headlining the 2005 Isle of Wight Festival and was replaced by Travis?
Morrissey
Morrissey had been due to top the Saturday bill; Travis stepped up, between Friday headliners Faithless and Sunday's R.E.M.
Q 30Which singer, the opening act at Woodstock, closed the 1970 Isle of Wight Festival as dawn broke?
Richie Havens
Richie Havens played on the morning of 31 August, and a cloudy dawn arrived during his version of Here Comes the Sun.