I parked at the little Bear Ridge pullout and crossed the street, uphill on the private road to a gated old logging road. Walk the old road for a few minutes and you'll see the access trail on your left. The trail switchbacks up past an old cabin in the woods (empty) and a couple neighborhood access trails before reaching the Mountainside Drive TH on Squak. I continued uphill and onto the Chybinski Loop. By this point there is snow on the trail, fairly packed and slushy/icy in places as well as the mudholes you should expect after as much rain as we've had lately. I continued up until I reached the turnoff for Margaret's Way. Margaret's way at first is in fine condition and was even run-able for me (I have a low tolerance for mud and slush/snow when running) and then became increasingly muddy in places with a couple of epic mudholes. At the Cougar/Squak corridor trailhead I headed north on SR900 for a short distance to the Cougar Mountain Wilderness Peak trailhead. I went to Wilderness Peak next, then back down the trail to Shy Bear Pass and down the trail towards Fred's Railroad trail. I followed this to Clay Pit Road, then across to Klondike Marsh, to Cougar Pass, then back to my car via the Tibbet's Marsh/Creek and finally Bear Ridge.
Overall, above about 1000 feet you should expect some snow. There was more snow on Cougar than on Squak- perhaps beacuse of different sorts of tree cover? the more open areas have more snow. However, I didn't step in any snow more than about 3" deep. As these trails get a lot of traffic and have been rained on for a couple of days, the snow was more of a slippery packed slush mixed with mud most of the time. I was fine in my trail runners, however, the weather forecast is for sub freezing temps this week. If you are headed this way after the hard freeze expected Tuesday, I would come prepared for all the wet slushy snow and mud to become ice.
This hike is a little over 13 miles and 3000+ elevation gain/loss.