At least 17 protesters were arrested and eight officers injured Wednesday as an "anti-capitalism" May Day march took a violent turn, first on Capitol Hill then in downtown Seattle.
Vandals shattered the glass door of Sun Liquor, at 512 East Pike, around 7 p.m. before heading downtown, hurling metal pipes and rocks at cars and police, shoving camera crews and setting off flares along the way.
Police say eight officers suffered scrapes and bruises clashing in the streets.
The crowd stopped briefly outside Niketown, but did not vandalize the business that was heavily targeted during last year's violent May Day riot.
Just before 8 p.m., police ordered the protesters to clear the streets, then deployed pepper spray and flash-bang grenades. Anyone who does not comply will be arrested, they said.
The chaos continued, however, as police attempted to control the unruly crowd. The protesters retreated back to Capitol Hill where some, using newspaper boxes, set up a makeshift road block and broke the windows of businesses, including a Walgreens store on Broadway and Pine.
The crowd gradually dispersed, in the next few hours, leaving behind shards of glass and trash strewn on the streets.
"We're a bigger and better city than this. I look at this and I am disappointed that this is the picture the world sees of us," said Seattle Mayor Mike McGinn late Wednesday night.

The marchers first gathered at Seattle Central Community College at 6 p.m. Because the organizers had not applied for a permit, it was not clear whether they had a predetermined route.
Shortly after the march began, the city's self-claimed superheroes, who had taken to the streets on a self-imposed mission to protect the city, were sprayed with silly string by several in the crowd. The costumed superheroes had briefly clashed earlier in the day with marchers dressed as clowns in downtown Seattle.
This is the second year in a row violence has broken out during May Day in Seattle. Last year, anarchists broke windows of storefronts, including Niketown, and vehicles and used smoke bombs. Protesters also targeted a federal building, breaking windows and doors.
Olivia One Feather of Covington joined the crowd Wednesday night because she wanted to see how police handled the protest. She said she wasn't impressed, adding that she was pepper sprayed in the face while trying to video record officers.
Of the protesters, she said, "They're doing what we need to do to stand up to ourselves. These are our streets and we have the right to take them."
Many of the protesters are self-described anarchists. A local anarchist website said protesters would attempt to disrupt May Day.
After the clashes died down, local residents were seen cleaning up trash left by the protesters.
The May Day violence capped a day of peaceful gatherings in Seattle and Olympia. In Seattle, thousands gathered at Judkins Park and marched to the federal building downtown in support of workers and comprehensive immigration reform. In Olympia, a peaceful march followed a family-friendly May Day celebration at Sylvester Park.