The 20 Most Iconic Sets at the Legendary 1969 Woodstock Music and Art Fair

Saturday’s second surprise act after Country Joe McDonald, Sebastian was fresh out of the Lovin’ Spoonful and working toward his first solo album, from which he previewed three tracks, along with two Spoonful favorites.

He told the crowd he was “freaked out” by its size, but Woody’s boy was in fine form nevertheless, covering Bob Dylan (“Walkin’ Down the Line”) — but unfortunately without enough time to play his signature epic “Alice’s Restaurant Massacree,” for what surely would have been an appreciative crowd.

The brass-rock group’s big lineup change from 1968 (swapping lead vocalists from Al Kooper to David Clayton-Thomas) was still reverberating, but a hit album and singles such as “Spinning Wheel” mitigated any of the turmoil — as did a strong performance that included a Joe Cocker cover (“Something’s Coming On”), nearly 12 hours after Cocker performed the original himself.

The New York singer-songwriter wasn’t on the festival bill; she just showed up and was slotted in to Friday’s acoustic-flavored lineup around the time of the rainstorm. It was quick-hit — just 25 minutes at 1:00 a.m. — but the crowd loved her. The experience inspired her first Top 10 hit, “Lay Down (Candles in the Rain),” and her first gold album, Candles in the Rain.

Ten Years After wasn’t the only blues-rock favorite to light up Sunday’s portion of the show. Winter ripped through a hot midnight set comprised of mostly covers, with younger brother Edgar Winter joining the group for three of its nine songs.

Booked because it, along with Dylan, defined the laid-back, rustic ethos of the actual Woodstock (where the group resided), there were high expectations for The Band’s Sunday night set after Ten Years After, and a lingering sense of disappointment that it ultimately wasn’t all that. A listen to the performance — including the full show on the 50th anniversary edition of The Band’s classic self-titled LP — says otherwise, however. The group members have acknowledged some wear and tear while waiting for its start time, but it still played songs from its first two albums with an unassuming (but crowd-pleasing) confidence.

With four albums already out (the latest, Hallelujah, arrived just a few weeks before the festival) the Los Angeles blues ‘n’ boogie troupe regaled the faithful with a set of lengthy jams, including the for-the-occasion “Woodstock Boogie” and a cover of John Lee Hooker’s “Rollin’ Blues.” Its “Going Up the Country,” meanwhile, became the subsequent film’s kick-off song.

Already an icon of the folk and protest movements that were so much a part of the Woodstock spirit, Baez — six months pregnant with son Gabriel — closed the first night in the wee hours of Saturday morning, with a 13-song set that covered Bob Dylan, The Byrds, Willie Nelson, Pete Seeger and The Rolling Stones. Baez warmed up by performing, unannounced, on the festival’s free stage after the Friday night rainstorm.

Talk about a set-up; the quartet had established local notoriety, but its debut album wouldn’t be Climbing! for another seven months. Nonetheless, Leslie West staked a claim as one of the best guitarists in Woodstock’s august ranks, raising Mountain’s stock exponentially — although to his dying day, he complained about Janis Joplin scarfing up the last bagel backstage.

Though “Going Home” is what lives on in split-screen glory in the film, the British blues-rock troupe played five other songs during an eclectic hour on stage, showing its ensemble strength beyond Alvin Lee’s lightning-fingered guitar heroics.

In the midst of a hit-filled three-album run, CCR was able to load its set up with favorites such as “Proud Mary,” “Bad Moon Rising” and “Green River.” “Keep on Chooglin’” and “Suzie Q,” meanwhile, showed that the quartet could jam with plenty of fire, too.

What exactly were a bunch of Columbia University students dressed up like 50s greasers, playing Danny and the Juniors hits doing at Woodstock? Entertaining those that remained into Monday morning, of course, with enough crazy choreography to make any festival goer surmise that those hand-out sandwiches may well have been dosed.

The first man on, somewhat reluctantly, got Woodstock started with a furious, passionate performance whose highlights — “Handsome Johnny,” covers of The Beatles’ “Strawberry Fields Forever” and “Hey Jude,” and an iconic medley of “Freedom” and “Sometimes I Feel Like a Motherless Child” — quickly planted a flag that something special was about to go down in Bethel.

The quartet’s second show suffered a bit for the late hour (3:30 a.m. Monday) and its own nervousness (“We’re scared s–tless,” Stephen Stills told the crowd), but the blend of acoustic and electric sets was a key part of launching a supergroup that would go on to great, and mythological, heights.

With festival organizers still getting their act together on the second day, McDonald was cajoled into getting the crowd ready for Santana on Saturday. His ad hoc solo set included the “Fish Cheer” (“Gimme an F!…”) and “Feel Like I’m Fixin’ to Die Rag,” fixtures for any Woodstock playlist. (He and his band The Fish returned for their scheduled performance on Sunday, which was delayed by that afternoon’s rainstorm.)

Not many knew who the British singer was when he and his Grease Band opened Sunday’s portion of the festival. By the time Cocker finished with his indelible, spasmodic take on the Beatles’ “With a Little Help From My Friends,” no one could forget him.

Tommy in its near-entirety, for a start; Pete Townshend whacking Abbie Hoffman off the stage with his guitar for a second. You couldn’t ask for a more eventful performance, with bookend rarities (“Heaven and Hell,” “Naked Eye”) that sometimes get lost in the shuffle.

With a new and under-rehearsed band, Hendrix’s closing set was admittedly shambolic. But if anybody’s going to pull off something still worthwhile out of such circumstances, it would be Hendrix. And turning “The Star Spangled Banner” into a psychedelic opus ensured that it would be legendary, regardless of any other shortcomings.

The rainbow coalition group from San Francisco wanted to take Woodstock higher, and it did — with a nine-song, wee-hours performance that brought Woodstock to life as assuredly as any good DJ does at a late-night rave in current times. 

The element of surprise gave this other Bay Area troupe an edge on Saturday afternoon. Some knew Carlos Santana from Al Kooper’s Super Session, but the release of his own band’s debut album was still a couple of weeks off. But the sextet killed it, putting some rocket fuel into a career that’s still going strong 55 years later.