Finding the Orphan Boy/Cooper Cabin
The Orphan Boy is a special place. First of all, if you haven't been there before, and you want to go in winter, you could be in for a significant challenge to find it. The trail will be almost completely obliterated by snow, and emerging at the correct spot after crossing down through the ravine is difficult. I tried to go there in winter three times, with no success, before going in the summer, when it was much easier to find. Once you have been there, winter route finding is a lot easier.
Three beginning routes are marked on the map below - from top to bottom: Pebble Creek trail (private ranch - you'll need permission to park), Old Wagon Road (leaves directly out the back of the parking lot on Rock Creek - now badly blocked by deadfall), and Rock Creek route (from Rock Creek parking lot to Gore Range Trail, then north). There is a 4th trail that leaves from the top of the Boss Mine dump and goes up to the ridge.
The route up the mountain follows the Old Wagon Road above the GRT. The intersection of the road and GRT is at the north side of the large wetland just downslope from the GRT, near the intersection of the conifer forest on the north and an aspen hillside on the south. In 2021, there were hundreds of trees down across the trail, but it is not difficult to stay on route.
Head up the Old Wagon Road - it starts with a hard, steep pull and continues up, up, up. Once on the ridge, you can begin to see up North Rock Creek Valley (~10,600'), ending with a nice rest spot (and downed log) with a view of the North Rock Creek headwall and summit of Mt.Keller (12,800'). Continuing on, you will pass a man-made ditch on your left that heads straight down the fall line. You are now directly above the Boss Mine tailings (the ditch was used to snake logs down to the mine, and it was a favored route by the Coopers). Continue on a short distance to the fork in the trail (in 2017, a tree fell right at the fork). The left fork goes up to timberline, the right fork goes to the Orphan Boy cabin. This trail gently climbs about 200', curving around to the left, and ends at the remains of a log cache (about 4' high).
You are now on the edge of the ravine, and will descend steeply nearly 400' through a stunning virgin spruce forest, crossing a small stream and an avalanche track - a big slide occured in ~2014, and it is easiest to work your way down along side of it until you can cross over. Then go up the hill a short distance and you will encounter the trail. Go right and soon you will arrive at the cabin.
The cabin is also accessible by hiking up Rock Creek to the Boss Mine, and taking the trail at the top of the tailings, up to the ridge. Another route is from Boulder Creek, and while the route is beautiful in its remote wildness, it is a steep and trailless slog.