The police tried to restrain some of the crowd, and knocked a few people down, which incited bystanders even more. Some of those handcuffed in the wagon escaped when police left them unattended (deliberately, according to some witnesses). As the crowd tried to overturn the police wagon, two police cars and the wagon—with a few slashed tires—left immediately, with Inspector Pine urging them to return as soon as possible. The commotion attracted more people who learned what was happening. Someone in the crowd declared that the bar had been raided because "they didn't pay off the cops", to which someone else yelled "Let's pay them off!"
Coins sailed through the air towards the police as the crowd shouted "Pigs!" and "Faggot cops!" Beer cans were thrown and the police lashed out, dispersing some of the crowd, who found a construction site nearby with stacks of bricks. The police, outnumbered by between 500 and 600 people, grabbed several people, including folk singer Dave Van Ronk—who had been attracted to the revolt from a bar two doors away from the Stonewall. Though Van Ronk was not gay, he had experienced police violence when he participated in antiwar demonstrations: "As far as I was concerned, anybody who'd stand against the cops was all right with me, and that's why I stayed in.... Every time you turned around the cops were pulling some outrage or another." en police officers—including two policewomen—barricaded themselves, Van Ronk, Howard Smith (a writer for The Village Voice), and several handcuffed detainees inside the Stonewall Inn for their own safety.
The Tactical Police Force (TPF) of the New York City Police Department arrived to free the police trapped inside the Stonewall. One officer's eye was cut, and a few others were bruised from being struck by flying debris. Bob Kohler, who was walking his dog by the Stonewall that night, saw the TPF arrive: "I had been in enough riots to know the fun was over.... The cops were totally humiliated. This never, ever happened. They were angrier than I guess they had ever been, because everybody else had rioted ... but the fairies were not supposed to riot ... no group had ever forced cops to retreat before, so the anger was just enormous. I mean, they wanted to kill."
Multiple accounts of the riot assert that there was no pre-existing organization or apparent cause for the demonstration; what ensued was spontaneous. Michael Fader explained,-
'We all had a collective feeling like we'd had enough of this kind of shit. It wasn't anything tangible anybody said to anyone else, it was just kind of like everything over the years had come to a head on that one particular night in the one particular place, and it was not an organized demonstration.... Everyone in the crowd felt that we were never going to go back. It was like the last straw. It was time to reclaim something that had always been taken from us.... All kinds of people, all different reasons, but mostly it was total outrage, anger, sorrow, everything combined, and everything just kind of ran its course. It was the police who were doing most of the destruction. We were really trying to get back in and break free. And we felt that we had freedom at last, or freedom to at least show that we demanded freedom. We weren't going to be walking meekly in the night and letting them shove us around—it's like standing your ground for the first time and in a really strong way, and that's what caught the police by surprise. There was something in the air, freedom a long time overdue, and we're going to fight for it. It took different forms, but the bottom line was, we weren't going to go away. And we didn't.'
The only photograph taken during the first night of the riots shows the homeless youth that slept in nearby Christopher Park, scuffling with police. The Mattachine Society newsletter a month later offered its explanation of why the riots occurred: "It catered largely to a group of people who are not welcome in, or cannot afford, other places of homosexual social gathering.... The Stonewall became home to these kids. When it was raided, they fought for it. That, and the fact that they had nothing to lose other than the most tolerant and broadminded gay place in town.
Garbage cans, garbage, bottles, rocks, and bricks were hurled at the building, breaking the windows. Witnesses attest that "flame queens", hustlers, and gay "street kids"—the most outcast people in the gay community—were responsible for the first volley of projectiles, as well as the uprooting of a parking meter used as a battering ram on the doors of the Stonewall Inn.
Sylvia Rivera, who was in full drag and had been in the Stonewall during the raid, remembered
"You've been treating us like shit all these years? Uh-uh. Now it's our turn!... It was one of the greatest moments in my life."
The mob lit garbage on fire and stuffed it through the broken windows as the police grabbed a fire hose. Because it had no water pressure, the hose was ineffective in dispersing the crowd, and seemed only to encourage them.When demonstrators broke through the windows—which had been covered by plywood by the bar owners to deter the police from raiding the bar—the police inside unholstered their pistols. The doors flew open and officers pointed their weapons at the angry crowd, threatening to shoot. The Village Voice writer Howard Smith, in the bar with the police, took a wrench from the bar and stuffed it in his pants, unsure if he might have to use it against the mob or the police. He watched someone squirt lighter fluid into the bar; as it was lit and the police took aim, sirens were heard and fire trucks arrived. The onslaught had lasted 45 minutes.
With larger numbers, police detained anyone they could and put them in patrol wagons to go to jail, though Inspector Pine recalled, "Fights erupted with the transvestites, who wouldn't go into the patrol wagon". His recollection was corroborated by another witness across the street who said, "All I could see about who was fighting was that it was transvestites and they were fighting furiously".
The TPF formed a phalanx and attempted to clear the streets by marching slowly and pushing the crowd back. The mob openly mocked the police. The crowd cheered, started impromptu kick lines, and sang to the tune of The Howdy Doody Show theme song: "We are the Stonewall girls/ We wear our hair in curls/ We don't wear underwear/ We show our pubic hairs".
Lucian Truscott reported in The Village Voice: "A stagnant situation there brought on some gay tomfoolery in the form of a chorus line facing the line of helmeted and club-carrying cops. Just as the line got into a full kick routine, the TPF advanced again and cleared the crowd of screaming gay power ites down Christopher to Seventh Avenue."
One participant who had been in the Stonewall during the raid recalled, "The police rushed us, and that's when I realized this is not a good thing to do, because they got me in the back with a night stick". Another account stated, "I just can't ever get that one sight out of my mind. The cops with the [nightsticks] and the kick line on the other side. It was the most amazing thing.... And all the sudden that kick line, which I guess was a spoof on the machismo ... I think that's when I felt rage. Because people were getting smashed with bats. And for what? A kick line."
Craig Rodwell, owner of the Oscar Wilde Memorial Bookshop reported watching police chase participants through the crooked streets, only to see them appear around the next corner behind the police. Members of the mob stopped cars, overturning one of them to block Christopher Street. Jack Nichols and Lige Clarke, in their column printed in Screw, declared that "massive crowds of angry protesters chased [the police] for blocks screaming, 'Catch them!'
By 4:00 in the morning the streets had nearly been cleared. Many people sat on stoops or gathered nearby in Christopher Park throughout the morning, dazed in disbelief at what had transpired. Many witnesses remembered the surreal and eerie quiet that descended upon Christopher Street, though there continued to be "electricity in the air". One commented: "There was a certain beauty in the aftermath of the riot.... It was obvious, at least to me, that a lot of people really were gay and, you know, this was our street."
Thirteen people had been arrested. Some in the crowd were hospitalized, and four police officers were injured. Almost everything in the Stonewall Inn was broken. Inspector Pine had intended to close and dismantle the Stonewall Inn that night. Pay phones, toilets, mirrors, jukeboxes, and cigarette machines were all smashed, possibly in the riot and possibly by the police.
During the siege of the Stonewall, Craig Rodwell called The New York Times, The New York Post, and The New York Daily News to inform them what was happening. All three papers covered the riots; The New York Daily News placed coverage on the front page. News of the riot spread quickly throughout Greenwich Village, fueled by rumors that it had been organized by the Students for a Democratic Society, the Black Panthers, or triggered by "a homosexual police officer whose roommate went dancing at the Stonewall against the officer's wishes".
All day Saturday, June 28, people came to stare at the burned and blackened Stonewall Inn. Graffiti appeared on the walls of the bar, declaring "Drag power", "They invaded our rights", "Support gay power", and "Legalize gay bars", along with accusations of police looting, and—regarding the status of the bar—"We are open".
The next night, rioting again surrounded Christopher Street; participants remember differently which night was more frantic or violent. Many of the same people returned from the previous evening—hustlers, street youths, and "queens"—but they were joined by "police provocateurs", curious bystanders, and even tourists. Remarkable to many was the sudden exhibition of homosexual affection in public, as described by one witness: "From going to places where you had to knock on a door and speak to someone through a peephole in order to get in. We were just out. We were in the streets."
Thousands of people had gathered in front of the Stonewall, which had opened again, choking Christopher Street until the crowd spilled into adjoining blocks. The throng surrounded buses and cars, harassing the occupants unless they either admitted they were gay or indicated their support for the demonstrators. Sylvia Rivera saw a friend of hers jump on a nearby car trying to drive through; the crowd rocked the car back and forth, terrifying its occupants. Another of Rivera's friends, Marsha P. Johnson, climbed a lamppost and dropped a heavy bag onto the hood of a police car, shattering the windshield. As on the previous evening, fires were started in garbage cans throughout the neighborhood. More than a hundred police were present from the Fourth, Fifth, Sixth, and Ninth Precincts, but after 2:00 a.m. the TPF arrived again. Kick lines and police chases waxed and waned; when police captured demonstrators, whom the majority of witnesses described as "sissies" or "swishes", the crowd surged to recapture them. Street battling ensued again until 4:00 a.m.
Beat poet and longtime Greenwich Village resident Allen Ginsberg lived on Christopher Street, and happened upon the jubilant chaos. After he learned of the riot that had occurred the previous evening, he stated, "Gay power! Isn't that great!... It's about time we did something to assert ourselves", and visited the open Stonewall Inn for the first time. While walking home, he declared to Lucian Truscott, "You know, the guys there were so beautiful—they've lost that wounded look that fags all had 10 years ago".