60 free Hard Woodstock trivia questions with answers — music quiz, new questions added Aug 2026.
This is the hard Woodstock trivia quiz. If you already know it happened on Max Yasgur's farm in Bethel, that Richie Havens opened and Jimi Hendrix closed, and that Joni Mitchell wrote the song without being there, these 60 questions go much deeper: the first band to sign a contract, the cowboy star asked to close the show, the guitarist who broke up his own band to avoid playing, the studio the financiers were really trying to build, and the couple on the soundtrack cover. The set covers the planning and the money, the acts who declined or missed the festival, the sound and lighting crews, the medical and security story, the Oscar-winning film and its editors, the soundtrack albums and box sets, Woodstock '94, '99 and the cancelled Woodstock 50, and what became of the site. It is written for people who have read The Road to Woodstock and Young Men with Unlimited Capital, not just watched the movie. Every answer was checked against a primary or encyclopedic source before publishing and each question carries its citation. For a warm-up, start with our main Woodstock trivia quiz and then come back for this one.
30 of 60 questions with answers and explanations. Play the quiz
Q 01Which band was the first act to sign a contract for Woodstock, in April 1969?
Creedence Clearwater Revival
Drummer Doug Clifford said everyone else jumped in line once they signed. The band later resented its 12:30 am slot and its absence from the film.
Q 02Which frontman kept his band out of the 1970 Woodstock film, feeling their set was unworthy?
John Fogerty
The band had gone on at 12:30 am after the Grateful Dead. An official Live at Woodstock album of all 11 songs finally appeared for the 50th anniversary in 2019.
Q 03Roughly how many advance tickets were sold for Woodstock before it turned into a free concert?
186,000
Tickets were only available at record stores in the New York area or by mail to a Radio City Station post office box. Gate price was to be $24.
Q 04What were John Roberts and Joel Rosenman building in Manhattan when approached about Woodstock?
A recording studio called Mediasound
Lang and Kornfeld wanted money for a smaller studio in Woodstock; Roberts and Rosenman counter-proposed a concert instead. Woodstock Ventures formed in January 1969.
Q 05Which Saugerties property, considered and rejected for the 1969 festival, ended up hosting Woodstock '94?
Winston Farm
Lang and Kornfeld wrongly believed they had secured it in 1969. Twenty-five years later it drew an estimated 350,000 people.
Q 06Which body of water formed the backdrop to the Woodstock stage and became a popular skinny-dipping spot?
Filippini Pond
The land formed a natural bowl sloping down to the water. Its owner was the only landowner who refused to sign a lease with the promoters.
Q 07Local opponents of the festival put up signs urging people to boycott what?
Max Yasgur's milk
One sign read 'Buy No Milk. Stop Max's Hippy Music Festival'. Yasgur was the largest milk producer in Sullivan County, with about 650 cows.
Q 08How many National Guard troops did Governor Rockefeller consider sending to the festival?
10,000
Roberts talked him out of it. Sullivan County declared a state of emergency, and Stewart Air Force Base helicopters ferried performers in and out.
Q 09Why did the 346 off-duty NYPD officers meant to handle Woodstock security withdraw?
A warning about breaking rules on moonlighting
The Hog Farm commune ended up as the 'Please Force', armed, in Wavy Gravy's words, with cream pies and seltzer bottles.
Q 10Introduced at Woodstock as the Experience, what did Hendrix say his group could be called?
A Band of Gypsies
The line-up was actually billed as Gypsy Sun and Rainbows. By the time he went on at 8:30 Monday morning the crowd had shrunk to about 30,000.
Q 11Besides two drug overdoses, the third recorded death at Woodstock was caused by what?
A tractor running over a sleeping teenager
The 17-year-old was asleep in a nearby hayfield. Despite claims, an author's extensive research could not confirm a single birth at the festival.
Q 12Which sound engineer built the Woodstock PA, nicknamed the 'Woodstock Bins'?
Bill Hanley
He designed the system for 150,000 to 200,000 people. Each half-ton plywood cabinet held four 15-inch JBL speakers.
Q 13The live performances at Woodstock were captured backstage in a tractor trailer on what equipment?
Two 8-track Scully recorders
Q 21Which television programme did Joni Mitchell's manager insist she appear on instead of playing Woodstock?
The Dick Cavett Show
She wrote her song 'Woodstock' in a New York hotel room watching TV reports and hearing Graham Nash's account. She first performed it at the Big Sur Folk Festival a month later.
Q 22Which singing cowboy star was asked to close Woodstock with 'Happy Trails' but declined?
Roy Rogers
Instead the festival ended with Hendrix on Monday morning. Rogers' regular closing theme had been written by his wife Dale Evans.
Q 23The Rolling Stones declined Woodstock partly because Mick Jagger was in Australia filming which movie?
Ned Kelly
Eddie Kramer and Lee Osbourne ran the tapes at 15 inches per second and later mixed them at the Record Plant in New York.
Q 14Which extra job was lighting designer Chip Monck handed at the last minute at Woodstock?
Master of ceremonies
Michael Lang realised he had forgotten to hire an MC. Most of Monck's rented lighting sat unused under a stage roof too weak to hold it.
Q 15Apple Corps offered which act to Woodstock by letter, just as the promoters were losing the Wallkill site?
The Plastic Ono Band
Michael Lang had invited John Lennon's new group knowing the Beatles were unavailable while recording Abbey Road. Nixon's government reportedly did not want Lennon in the country anyway.
Q 16Which guitarist said he deliberately broke up his band before Woodstock because he did not want it 'preserved'?
Jeff Beck
His pianist Nicky Hopkins ended up performing with Jefferson Airplane instead. Beck was booked for Woodstock '99 too, and cancelled that as well.
Q 17Bill Graham forced Chicago out of Woodstock so which band he managed could take the slot?
Santana
Graham also won a coin toss with Michael Lang over whether It's a Beautiful Day or Santana would play. Santana's debut album had not even been released.
Q 18Which Doors member appeared as a guest with Creed at Woodstock '99?
Robby Krieger
Krieger and Densmore had attended the original festival as spectators. Krieger said the band feared a second-class repeat of Monterey Pop.
Q 19Bob Dylan planned to sail to England on August 15, 1969, the day Woodstock began, but disembarked. Why?
His son was injured by a cabin door
Dylan lived in the town of Woodstock but never seriously negotiated to appear. He flew to England the following week and played the Isle of Wight Festival with the Band.
Q 20Which band on the Woodstock Sunday poster never played, stuck at LaGuardia demanding helicopters?
Iron Butterfly
Production coordinator John Morris replied with a telegram whose lines spelled out a rude acrostic telling them to find other transportation.
Keith Richards' girlfriend Anita Pallenberg had also just given birth to their son Marlon. Four months later the Stones headlined the disastrous Altamont concert.
Q 24Which pop star turned down Woodstock after his secretary called it a 'pig farmer' who 'wants you to play in his field'?
Tommy James
Tommy James and the Shondells were in Hawaii at the time. James said they realised what they had missed a couple of days later.
Q 25Which New York Times editorial headline compared Woodstock's crowd to lemmings marching into the sea?
Nightmare in the Catskills
The other two headlines belonged to the Daily News. Coverage turned positive partly because parents phoned the media after hearing from their children at the site.
Q 26How did the Middletown Times Herald-Record get Woodstock stories and photos to its office 35 miles away?
By motorcyclist
The paper had editorialised against the Wallkill ban and printed a rare Saturday edition during the festival.
Q 27Which Warner Bros. executive put his job on the line to give Artie Kornfeld $100,000 to film Woodstock?
Fred Weintraub
Kornfeld had been turned down everywhere else. The film is credited with helping save Warner Bros. when the studio was close to going under.
Q 28How did director Michael Wadleigh pay his roughly 100-person film crew at Woodstock?
A double-or-nothing deal tied to box-office success
The crew would get double pay if the film succeeded and nothing if it bombed. It grossed about $50 million on a $600,000 budget.
Q 29Which Woodstock editor earned a rare Academy Award nomination for Best Film Editing on a documentary?
Thelma Schoonmaker
She headed the editing crew and went on to a lifelong partnership with fellow editor Scorsese, winning three Oscars for his films.
Q 30How long is the 1994 director's cut of the Woodstock film?
224 minutes
The 1970 release ran 185 minutes. The longer cut added Janis Joplin plus more Jefferson Airplane, Hendrix and Canned Heat.