Snowed in for winter. Keep your dog on a leash or under control.
Run through the parking lot of Timberline Lodge, past the swimming pool and amphitheater on your right, and the Magic Mile lift on your left. Start on the Mountaineer/Timberline to Town Trail on your left. Follow Mountaineer for about 1,500 feet past the pool until Timberline to Town breaks off on your left as you enter a ski run. From there, you'll pass through 4 consecutive ski runs and then head into the woods. There are some good photo ops with Mt. Hood in the background in the ski runs.
About 1.3 miles in, you cross back to the east side of the old Glade Ski Trail. As you go lower, there are some tighter corkscrew turns and vestiges of the old Blossom Ski Trail as well as the corridor that had a ski lift mounted city bus used as a gondola between Government Camp and Timberline from the 1950's to 1962. The trail should be distinguishable from these other routes.
Just as you cross the old Glade Trail opening, you reach the intersection with Crosstown Trail. At this point there is hiker/biker congestion and less visibility, be aware of riders on the hill. You can continue across Crosstown Trail a short way on the old Glade Trail and that puts you out on East Blossom Trail Way Road which can be followed into downtown.
Please do not park or stage cars at the end of this road as there is not trailhead parking and the local residents on that road will become upset.