A small group of plain clothes police raided the Stonewall Inn with the intent to arrest anyone they determined were “cross-dressing.” This was a standard practice in most US cities.
There was actually no specific law against cross-dressing. Police departments tended to use archaic laws about concealing one’s face in public and other unrelated statutes when processing arrests. Raiding bars and other places where gay people congregated, and the harassment and brutality used to execute them, was not about upholding any laws, but a social norm that gay and queer people live closeted lives, keeping their real selves out of public view. As social conventions like this one and Jim Crow were increasingly challenged throughout the 1950s, police increasingly had to enforce heteronormalcy with arrests and violence, where in the past stigma and shame had kept gay people in line.
During the raid at Stonewall on June 28, 1969, police encountered a crowd they were not prepared to deal with. Instead of fearful compliance and attempts of arrestees to conceal their faces on the way to jail, the raid was met with a defiant crowd unafraid of drawing attention from bystanders outside or challenging the arresting officers. The throngs of bystanders grew and many began to join in jeering the police and eventually throwing objects at them. As police lost control of the situation, they retreated inside the Stonewall Inn and called for reinforcements. It took them until 4am to clear the streets, and a second riot broke out the next evening.
Organized resistance to police raids and other acts of homophobic oppression preceded Stonewall, but the event was a tipping point in the movement to end the status quo. The first gay pride marches were organized in 1970 on the anniversary of the Stonewall riots.
Sources:
They Stonewall you know is a Myth, and that’s OK- New York Times
June 28, 1969: The Stonewall Riots- Zinn Education Project
Stonewall Riots: Eye-witness account- National Law Enforcement Museum
How Dressing in Drag was labeled a Crime in the 20th Century- History Channel