When I first arrived, there were maybe 1000 people in the parks and on the surrounding corners, particularly across SW 3rd Ave, watching from the coverings of the buildings. The cops circled the blocks, making their rounds but interacting minimally with the crowd except for occasionally to tell people to get out of Main Street between the two main encampment blocks.
Around 11:45pm, the crowd began occupying Main Street once more. The cops had pulled back to the 3rd and 4th avenue, leaving Main. When it turned midnight, people began counting down to 12:01am since that was the announced deadline for people to evacuate the park by the city. At the bottom of this page is a link to the video of the people approaching 12:01am like it was New Years.
After the countdown, the atmosphere became more jovial. We had called them on their bluff and were victorious. People began to relax, spread out and possibly leave. However, our numbers continued to increase. I would estimate that there was around 3000 people there at certain times and 3000-5000 people in and out of camp throughout the night.
Close to 1:30am, the cops began lining the intersection of 3rd and Main with the riot gear and their horses. A woman walked by me who had gotten punched in the face by a cop. I saw another person receiving help from the medics after the cops pepper-sprayed him. Other people, including medics, talked about how the spray had hit them as well. The cops then pushed their horses in the the crowd at 3rd and Main in the middle of Main. People yelled that they were being peaceful and even held up the peace fingers. However, they pushed back against the cops, not letting the horses shove their fellow protesters around.
After enduring 30 minutes of the cops' hostilities and intimidation, they backed down. The horses retreated and the people took 3rd Ave. A bike brigade continued to circle the blocks all night, inspiring cheers throughout the crowds. Again, people most likely left when things appeared to be peaceful but the bar crowd arrived after the bars shut down. Still, there was no incidents of drunken or rowdy behavior from the crowd, just solidarity.
Around 4:30am at 3rd and Madison, the cops again put up a wall of riot cops and horses even though the horses stayed back this time from the crowd. The cops were seen brandishing less lethal weapons inside their wall of riot cops. The crowd again yelled peace but again surged to the front lines. The standoff remained a draw until shortly after 5am, when it was presumed that the parks would be legally open to occupy. (On a side note, that doesn't mean you're safe. I've seen cops "close down" parks and arrest people in the middle of the day.)
Less than half of the crowd went back to the park and the drum circle remained in the intersection of 3rd and Madison as the cops again fell back. When the sun came up, the cops were gone, the people were again in the park, the intersections were clear and this witness went to bed.
When I awoke this morning, I looked at my neighbors and random people on the street differently. At the protest last night, I saw not only my known comrades but also a wide spectrum of people. Even at 6am, I saw people of various apparent classes, ages, races, etc. I thought to myself then that this is a shared historic moment that thousands of Portlanders have now. After I awoke later, I saw people walking about that very well could have been a part of yesterday's events. Not only are these my neighbors now but they are also community.