On July 20, 2020 large groups of people gathered in downtown Portland in Chapman Square Park and Lownsdale Square Park and in Waterfront Park near the Salmon Springs Fountain. At about 9:00 p.m. the crowds converged on SW 3rd Avenue outside the Justice Center and gave speeches. Cars, motorcycles and bicycles blocked streets around the crowd.

At about 10:15 p.m. the crowd walked through downtown streets eventually returning to the area of the Federal Courthouse around 11:30 p.m. The crowd grew and people began spray painting the Justice Center and Federal Courthouse. People tampered with and climbed on the gate leading under the Justice Center and pounded on plywood on the exterior of the building. They behaved similarly at the Federal Courthouse.

Several hundred people concentrated on the west side of the Federal Courthouse and dozens of them pounded on and began breaking the plywood covering the west side of the building. People were using hammers, crowbars and other pry tools. Many people could be seen carrying bats and shields, people wore helmets and gas masks. At about 12:45 a.m. on July 21, 2020, people broke through the plywood outside the courthouse and started pounding windows with metal objects, breaking at least one window. Hundreds of people were packed tightly in the portico on the west side of the courthouse pushing toward the entrance.

At about 12:38 a.m. federal law enforcement began dispersing the crowd using a variety of munitions. Many people in the crowd threw rocks, bottles, and other projectiles at the federal officers. People scattered into the surrounding blocks over the next twenty minutes. At one point a group of about seventy five people holding shields lined up across SW Main west of SW 3rd. They moved slowly toward the middle of the intersection but eventually broke up.

By 1:30 a.m. there were a few dozen people back on the courthouse portico throwing glass and plastic bottles, wood, pieces of metal, rocks and other debris at the building. People also lit fires in garbage cans, and near a tree by the courthouse.

At about 2:24 a.m. people lit a fire near a door on the SW Salmon Street side of the courthouse. Federal law enforcement put it out. At 2:29 a.m. people poured an accelerant on the plywood over the door on the front of the courthouse and ignited it. Federal officers dispersed the crowd using various munitions.

At 2:45 a.m. several dozen people blocked off SW Salmon Street at SW 5th Avenue with fencing and an assortment of other material stolen from nearby properties. People continued to light fires downtown including a fire on the awning and side of a building, at SW 4th Avenue and SW Yamhill Street, which required Portland Fire & Rescue to respond. At about 3:00 a.m. another fire was burning in the middle of the sidewalk north side of the County Courthouse, which required Portland Fire & Rescue response. Before they arrived people continually added flammable material to it causing it to grow and burn against the building. Portland Police responded to provide security for firefighters.

While Portland Police Officers were in the area of the County Courthouse a person threw a glass bottle at them, then fled.

At about 3:07 a.m. a caller reported that people had broken into a jewelry store in the 500 Block of SW 3rd Avenue. Portland Police responded and found the windows broken out and could see that valuables had been removed. Officers searched the area for the suspects. A vehicle fled the scene as officers investigated.

A caller reported that windows at City Hall were broken out.

Portland Police Bureau officers did not deploy CS gas and made no arrests.