Details about how the riot started vary from story to story. According to one account, a transgender woman named Sylvia Rivera threw a bottle at a police officer after being prodded by his nightstick (Duberman). Another account states that a lesbian, being brought to a patrol car through the crowd put up a struggle that encouraged the crowd to do the same (D’Emilio 232). Whatever the case may be, mêlée broke out across the crowd—which quickly overtook the police. Stunned, the police retreated into the bar. Heterosexual folk singer Dave van Ronk, who was walking through the area, was grabbed by the police, pulled into the bar, and beaten. The crowd’s attacks were unrelenting. Some tried to light the bar on fire. Others used a parking meter as a battering ram to force the police officers out. Word quickly spread of the riot and many residents, as well as patrons of nearby bars, rushed to the scene.
Throughout the night the police singled out many transgender people and gender nonconformists, including butch women and effeminate men, among others, often beating them. On the first night alone 13 people were arrested and four police officers, as well as an undetermined number of protesters, were injured. It is known, however, that at least two rioters were severely beaten by the police (Duberman 201-202). Bottles and stones were thrown by protesters who chanted “Gay Power!” The crowd, estimated at over 2000, fought with over 400 police officers.
The police sent additional forces in the form of the Tactical Patrol Force, a riot-control squad originally trained to counter Vietnam War protesters. The tactical patrol force arrived to disperse the crowd. However, they failed to break up the crowd, who sprayed them with rocks and other projectiles.
Eventually the scene quieted, but the crowd returned again the next night. While less violent than the first night, the crowd had the same energy as it had on the previous night. Skirmishes between the rioters and the police ensued until approximately 4:00 a.m.. The third day of rioting fell five days after the raid on the Stonewall Inn. On that Wednesday, 1,000 people congregated at the bar and again caused extensive property damage.
“Queen power reared its bleached blonde head in revolt. New York City experienced its first homosexual riot. … The crowd began to get out of hand, eye witnesses said. Then, without warning, a gay atomic bomb. Queens, princesses, and ladies in waiting began hurling anything they could lay their polished, manicured finger nails on. … The war was on. The lilies of the valley had become carnivorous jungle plants.”
New York Daily News, Homo Nest Raided, Queen Bees Stinging Mad