There are a lot of different trails to go on at this location, so make sure to take a picture of the map at the trailhead or download one beforehand. It is easy to get turned around but there are signs marking the different trails. On the day we went on this hike, the trail was mostly clear of obstacles except for a lot of puddles and mud.
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Even a simple place like Cougar Mountain can become a winter wonderland! We started at the Wilderness Peak Trailhead with the trail being pretty slick in the first half mile because of how well used the trail was, making it icy. On our way down the ice melted into slush. But if it refreezes at night, be careful. We and hiked up the Wilderness Cliffs Trail up Wilderness Peak. As we got away from the well-used parts of trail, the fresh powdery snow was pretty nice on the trail. Then from Shy Bear Pass we hiked Fred's RR and East Fork Trails to the big mine shaft and the clay pit. We hiked Cougar Pass and Anti-Aircraft Ridge Trails up to the viewpoint of Lake Sammamish at the Harvey Manning TH. We then followed the road from the parking lot up to the top of Anti-Aircraft Peak and hiked down the Lost Beagle and Coyote Creek Trails, then down the Cave Hole Trail and then to Coal Creek Falls. The waterfall and creek were amazing in the snow. We hiked back up Quarry Trail back up to Shy Bear Pass, and down Wilderness Creek to the TH. The more traveled sections of trail are icy of slushy and microspikes could be helpful. But the lesser used sections were great and easy to hike on.
Christmas Eve urban hike. Started late morning, many empty spots in the parking lot at the Red Town Trail Head. Hiked to the Coal Creek Falls via Quarry and Shy Bear trails, and returned via Cave Hole trail. Encountered several people - although, parts of the Shy Bear trail are not as traveled, it seemed. Many more trails in this area yet to be explored by this CityBoyHiker. It was cold, but dry. Lovely Christmas Eve hike!
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I couldn't wait for the rain to stop, so I went for a short hike to the falls while it poured. Only saw two other parties in the parking lot and on Redtown, so it was a quiet walk. I took Redtown to the Indian trail, then hopped on the Quarry trail to get to the Falls. I looped around and ended up on the Cave Holes trail and back on Redtown to the leave. Quarry and Coal Creek Falls trails were saturated with water and had some bigger puddles to maneuver, but it wasn't muddy or too slippery at all. The Falls were beautiful; I wish I could've stayed longer.