PORTLAND, Ore. (KOIN) — Federal authorities again used tear gas, flashbangs and other crowd-control munitions against protesters in downtown Portland after the largest crowd the city has seen in recent weeks gathered on Monday night for the 53rd consecutive night of protests against police brutality.

KOIN 6 News witnessed protesters and the federal officers face off near SW 3rd and Main, and saw authorities use pepper balls and throw tear gas canisters and flashbangs. Meanwhile, Portland police reported on social media hundreds of protesters had scattered to surrounding streets and that some were “throwing projectiles” and were “armed with clubs hammers and other weapons [sic].”

The Portland Police Bureau said that demonstrators attempted to break into the federal courthouse in the early hours of Tuesday morning, prying back plywood while donned in helmets, gas masks and shields. Protesters reportedly used crowbars and other tools to penetrate the makeshift wooden exterior, breaking at least one glass window — before being rushed by federal officers deploying tear gas once again.

Police report several fires were lit outside and around the federal courthouse overnight and Portland Fire and Rescue crews were required to respond multiple times. One nearby jewelry store, H & B Jewelry & Loan Company, was broken into and reportedly robbed.

Additionally, City Hall saw multiple windows broken overnight.

It’s unclear if any demonstrators were arrested or detained by federal officers. PPB says they did not make any arrests or use tear gas overnight.

Before federal officers used force against the protesters, a movement of moms and dads drew hundreds of parents dressed in yellow and orange, respectively, first to Salmon Street Springs, and then to the federal courthouse and neighboring Justice Center.

People have been galvanized by the presence of federal officers, who were deployed by President Donald Trump to protect federal property and have had their presence and use of force tactics condemned by local and state leaders.

More than 1000 people had gathered on SW 3rd Avenue by 10 p.m. Individuals took turns speaking to the crowd, which responded with cheers and echoed chants. At one point, demonstrators broke out in song: “If Black lives matter, clap your hands.”

Timeline of Events

3 a.m.

Another fire was lit outside the County Courthouse around 3 a.m., again requiring Portland Fire and Rescue to respond. Protesters continuously added flammable materials, growing the fire and making it burn near the building, police say.

Shortly after 3 a.m., a break-in at H & B Jewelry & Loan Company was reported. When officers arrived, they found broken windows and saw merchandise had been stolen. While investigating, police say a car fled from the scene.

No arrests were made.

2:30 a.m.

A fire was lit on the side of the federal courthouse shortly before 2:30 a.m. on Tuesday morning, according to police. Federal officers reportedly extinguished the fire, just for protesters to pour an accelerant on the building’s plywood and ignite once more.

Feds then dispersed the crowd once again.

By 2:45 a.m., police say multiple fires had been lit around the area, including one that Portland Fire and Rescue was required to come in and knock down.

1 a.m.

Protesters and federal officers continued to face off around the federal courthouse and in the surrounding parks. Authorities used pepper balls and flash bangs in addition to throwing canisters of tear gas as they worked to repair a damaged boarded door to the courthouse, while protesters shouted and kicked the canisters back.

By 1:30 a.m., federal authorities had returned to the confines of the courthouse. KOIN 6 News witnessed some protesters cheer and throw some items at the building, to which federal officers responded by shooting pepper balls through a hole in the plywood.

12 a.m.

Federal authorities used tear gas and other crowd-control munitions against protesters after rushing out of the courthouse around 12:30 a.m. when some protesters banged on a boarded-up door to the courthouse and peeled back some of the plywood, driving hundreds of demonstrators away from the Justice Center and federal courthouse area.

Police report demonstrators used hammers, crowbars and other pry tools to penetrate the plywood. They say people could be seen carrying bats and shields as people wore helmets and gas masks. Protesters reportedly broke one window.

11 p.m.

Demonstrators marched to the area of Pioneer Courthouse Square. They stopped in front of the murals at the Apple Store for a moment of silence. They then march back to the federal courthouse on SW 3rd Avenue.

Once demonstrators returned to the federal building, people stood at the front entrance and chanted to the beat of a drum in the crowd. In contrast to previous nights, there was no fence lining the perimeter of the building that kept people at a distance.

10 p.m.

Shortly before 10:30 p.m. people organized and prepared to march away from the Justice Center. A white pickup truck with speakers standing on the bed led the way.

People with microphones led the chants and the march up Madison Street away from the parks and Justice Center.

9 p.m.