The annual Halloween promenade down State Street turned ugly early Sunday morning when, for the first time in nearly 30 years, the Madison Police Department deployed tear gas and used pepper spray downtown to help quell a riot involving hundreds of people, which left students and police injured and storefront windows smashed.

The commotion evoked memories of Madison war protests of the 1960s, according to Lt. Cameron McLay of the Madison Police Department.

“This was the first time since anti-war demonstrations that Madison police have deployed tear gas in a crowd-control situation,” McLay said.

Amid an estimated costume-clad crowd of 65,000 packing State Street Saturday, bottles thrown by partiers in the direction of police officers sparked a violent confrontation between rioters and police officers.

Police arrested at least 16 on charges including looting, disorderly conduct and battery, according to McLay, who described Saturday night’s events as “a gradual escalation of isolated incidences of violence and destructive behavior.”

The windows of around half a dozen State Street businesses were broken during the riot, including Jamba Juice, Badger Liquor, Subway, the Chocolate Shoppe and Yellow Jersey bicycles. Badger Liquor and Princess of India Imports, both on the 600 block of State Street, reported missing inventory Sunday after rioters broke windows and stole merchandise.

Abdul Lababidi, owner of Princess India Imports, said he was awaken at six in the morning by a telephone call from police informing him his business had been robbed.

“They took stones [from Lisa Link Peace Park] and used them to break the windows,” Lababidi said. “And not just my window, but the whole block, including the bus shelter.”

Vimal Patel, owner of Subway on the 600 block of State Street, said he was glad the damage to his store was not more extensive, but called the rioter’s actions “stupid and pointless.”

The police department made the decision to don riot gear after rioters pelted officers with bottles and other debris while attempting to evacuate a reveler injured after interfering in a fight in front of Blockbuster Video on the 500 block of State Street, McLay said.

“The crowd was throwing debris towards cops and towards the victim laying flat on the ground,” said Ald. Mike Verveer, District 4, who witnessed the riot. “Ultimately, paramedics were able to get in, get him out on a stretcher.”

Rebecca Roblin, a University of Wisconsin student who watched the riot erupt from the balcony of her State Street apartment, estimated the number of riot participants at upwards of 300.

“I saw someone injured lying down in the middle of the street surrounded by blood. It took a long time for the paramedics to come,” Roblin said. “It was nuts. I was shocked to see how they were treating people, hitting kids.”

McLay said eight officers hit with concrete blocks and bottles reported injuries of varying severity.

Anticipating Halloween festivities to peak Oct. 31, 40 police officers patrolled State Street Saturday night, 110 fewer than Thursday night. Verveer said the difference proved fatal in the police’s inability to contain the crowd.

“Thursday night went off with a hitch — relatively no problems,” Verveer said. “Saturday night was a truly unfortunate experience, with the problem stemming from a small number of troublemakers, fueled in part by alcohol.”

Both Verveer and Roblin are confident the majority of riot participants were out-of-town visitors.

McLay, who has served in the Madison Police Department for 18 years, said he has never witnessed a Madison Halloween celebration as unruly as the incident Saturday night.

“Crowds used to be bigger than they have been in recent years, but never did it turn violent towards police as it did [Saturday] night,” McLay said.

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