As a downhill trail, the Upper Winsor Trail
starts above the ski area parking lot at the Pecos Wilderness Gate. If you'd like to ride this portion of the trail you'll have to climb up first. When you get to the gate, you'll have to stop and turn around (as bicycles are not allowed in the wilderness, or consider the almost impossible Raven's Ridge
climb - which is better as a descent).
On the way down, you'll find that the trail is fairly smooth and steep and can be very fast. Be very careful with hikers and PLEASE give them the right of way (which is not only polite, but is standard trail etiquette) as this trail has always been a "hiker-first" trail since it leads to the wilderness area.
Once you get back to the ski area parking lot, you can continue down, just past the outdoor toilets. You'll quickly get to a fork in the road where the Winsor splits off to the left over a bridge. To the right is the beginning of the Rio en Medio Trail.
Cross the bridge and continue on the trail, which will now begin to alternate between climbs and descents, ultimately ending with a tough climb up to the parking lot where most folks start the more common Winsor Trail
descent in earnest.