Portland police arrested 23 people during an anti-racism demonstration that brought up to 1,000 people into city streets Monday evening and lasted into the early-morning hours.

The protesters amassed outside the Portland police station in a confrontation that moved around the downtown area and lasted until nearly 2 a.m., police said. Officers from 15 other police departments joined Portland police and stood shoulder-to-shoulder carrying wooden batons and plastic riot shields.

Everyone arrested during the demonstration posted bail by Tuesday morning, said police spokesman Lt. Robert Martin. All but one person was charged with failure to disperse, a misdemeanor. One man, the driver of a tractor-trailer truck that entered the protest area near the intersection of Middle and Franklin streets, was charged with reckless conduct with dangerous weapon, a class-C felony.

Throughout the night, there was a push and pull between organizers who sought to keep the demonstrations peaceful, and people who threw water bottles and other objects at police, destroyed property and defaced businesses. At one point, some police knelt with protesters, drawing cheers from the crowd. Others talked with protesters from the police line, but most officers remained silent or did not react or engage.

Chief Frank Clark released a statement Tuesday afternoon in which he expressed disgust at the killing of George Floyd, the 46-year-old Minneapolis man who died in police custody when an officer pressed his knee into Floyd’s neck for nearly nine minutes, until he lost consciousness and stopped breathing. But Clark said a smaller segment of demonstrators was determined to cause trouble, leading to the harsher response by officers.

“Our goal remains providing a safe environment for those wishing to peacefully express their views and First Amendment rights,” Clark said in the statement. “We are fortunate that no one was seriously injured and that most of the property damage was minimal. Unfortunately a committed smaller segment of this group ended up making this event anything other than a peaceful and lawful protest. They took the opportunity to commit acts of violence, damage public and private property and place my officers and the public at risk. We will not stand for such criminal behavior.”

Attempts to reach the demonstration’s organizer, David Thete, were unsuccessful Monday evening. A number for Thete was no longer accepting incoming calls, and a message sent to him on social media was not returned.

Police say demonstrators on Monday night threw rocks, bottles, bricks and urine at police, and several trash cans were set on fire in the Old Port. Around 9 p.m. as night fell, demonstrators at one point encircled two police vehicles near the station and began striking them, Martin said. Demonstrators threatened police with death, police said in the release.

Four businesses were burglarized and five had windows broken or saw other acts of criminal mischief; officers also cited two dozen instances of graffiti in the Old Port area.

As the night progressed, cars revved their engines and sped down empty streets. Some passing motorists honked in support of the demonstration, while others antagonized them – one man driving a large black pickup truck reached out from his open window, made the shape of a gun with his fingers and mimicked shooting a group of young black men standing on a corner, two blocks from the epicenter of the confrontation, before driving off.

Police said one officer was struck in the face with a water bottle but did not need medical attention, and a small number of demonstrators who were sprayed by officers with pepper spray required assistance from paramedics.

The demonstration began peacefully, with hundreds staging a die-in on Middle Street in front of the police station. Protesters re-established a makeshift memorial on the police department steps dedicated to those who have been killed by police across the nation.

“There’s no bright line. We don’t say, ’10 o’clock we open the road back up,’ ” Martin said. “If it stayed peaceful for several more hours, I don’t think anything would have happened. There were trash cans set on fire and they were encircling police cars and trying to break police car windows.”

Martin estimated there were more than 100 officers on the scene, including many called from neighboring departments, the Cumberland County Sheriff’s Office, and the Maine State Police. The Maine Department of Transportation shut down Exit 7, which leads to Franklin Street and the epicenter of the confrontation, in both directions.

Cumberland County District Attorney Jonathan Sahrbeck said he will be reviewing police reports and other information before making a decision on how to proceed with any charges.

“We are still going to be looking at the cases and making sure that we get all the information we can before we make any charging decisions at the DA’s office,” Sahrbeck said Tuesday. “So we don’t know exactly how we’re going to proceed at this time.”

In 2016, a group of 17 Black Lives Matter protesters were arrested after a march in Portland. But a plea deal between the protesters and then-District Attorney Stephanie Anderson fell apart because the parties could not agree on the terms of a restorative justice meeting. A judge later denied Anderson’s attempt to restore the criminal charges, and the prosecutor did not pursue a meeting further.

Sahrbeck said he was not yet sure whether restorative justice would be the right approach in these cases.

“Obviously that didn’t work out as the parties initially thought it would,” Sahrbeck said. “I’m never going to rule out anything on day one. Restorative justice is something we’re trying to use a lot more in my office right now.”

The clash with Portland police was one among hundreds of rallies across the country involving millions of Americans on Monday night. Not since the civil rights movement of the 1960s has the United States seen such widespread urban uprisings that organizers say are a reaction to decades of unrelenting, systemic racism and police forces that operates with impunity, even when officers kill and maim the citizens they’re sworn to protect.

The arrest tally eclipses the 18 demonstrators who were charged in 2016, after a group protesting the killing of two black men in Baton Rouge, Louisiana, and in a suburb of St. Paul, Minnesota, blocked traffic along Commercial Street in the Old Port on a busy Friday night. Those charges were eventually dropped after a disputed restorative justice meeting fell apart before it could begin.

This story will be updated.