This all happened as thousands gathered to watch the annual Rockefeller Center Christmas tree lighting.
Watch Ali Bauman's report
The NYPD was expecting the demonstration and amped up security in response, knowing it would be a chaotic scene with a rally right next to the tree lighting.
But despite the provisions, demonstrators were able to break through their barricades and at some points even surround and physically fight with police.
One person faces a felony charge of criminal mischief, and six others were issued desk appearance tickets for obstructing governmental administration. A 15-year-old was also issued a juvenile report.
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NYPD officers sprinted through Sixth Avenue, where police clashed with demonstrators off 47th Street, blocks away from the annual tree lighting.
"This is the ebb and flow of protests. We try to keep it calm, we let them move, we let them exercise their right. Sometimes things get a little hectic, but we're gonna do our best out here to keep everybody safe," NYPD Chief of Department Jeffrey Maddrey said.
More than 1,000 people gathered for the demonstration in support of Palestinians. Earlier, organizers told CBS New York they anticipated a peaceful night.
"All we're asking for is an end to the ongoing bombing of Gaza, the end to the siege and blockade that continues to place a chokehold on the Palestinian people," said Nardeen Kiswani, with Within Our Lifetime.
But arrests swiftly began, starting with a fight breaking out over someone holding up a sign of a swastika.
Throughout the night, the NYPD tried to contain the group by holding lines and putting up barricades, but tensions escalated, reaching a boiling point when some demonstrators and officers squared off, throwing fists and falling to the ground.
"Crowd came and attacked, and it was a melee," one witness said.
Eventually, the barricades and cops could not contain the crowd. People broke through and began marching through the streets while officers continued to make one arrest after another.
Police said this did not disrupt the nearby tree lighting celebration.
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