The best map we have found that indicates this trail is "Map of the Mountains of Silverton, Telluride and Ouray" by Drake Mountain maps; reprinted in 2002. The FS Topo 2016 also does a good job, but the multiplicity of trails around Sheep Creek can make things confusing. Please note that this report is from a 2007 trip. Once you head north up the main fork of Deep Creek, things may have changed substantially - especially 2019 avalanche damage.
Take the road to the Telluride airport and continue past the airport turnoff to park at the Deep Creek/Whipple trailhead at about 9,060 on the Gray Head quad. The trail makes a few switchbacks up the open hillside before intersecting an old irrigation ditch which it follows north to where it crosses Sheep Creek. The trail number is 418. After crossing Sheep Creek (a rather minor flow) the trail heads due west still following the ditch. You will come to an intersection where a sign indicates the turnoff for the "Whipple" trail and provides a mileage of 2 miles. This trail departs the ditch and heads downhill along the crest of a gambel oak covered ridge. After losing some elevation, it begins contouring north again and gradually drops to cross the main east fork of Deep Creek that drains the valley below Mears Peak. A log footbridge provides access across the creek. The trail then climbs uphill a little before continuing west. It then drops along an old roadbed before reaching a sign marking private property. At this point, the trail departs the roadbed and begins heading in a more northerly to NW direction and well above the main fork of Deep Creek on the east side.
Follow this trail north until it passes the wilderness boundary sign (so worn it can't be read) and finally crosses the main fork of Deep Creek to the west side and then climbs uphill. The trail will take you through an open, grassy meadow (passing two old signposts) and switchback up an open, aspen covered hillside to emerge onto a nice sloping meadow. A trail sign here indicates the junction of trail 418 (the Deep Creek trail) and 419 (the Whipple Mtn. trail). Head straight ahead from this sign and enter a forested area. (From this point on, the trail is fairly visible, but there are places farther up where it will become more difficult to follow. It is frequently marked by cairns though to help you get back on track.) The trail will cross a minor creek in the forest, come to a small open area and then begin a steep climb up a hillside where several shortcut trails head off to the right. Stay on the most used path which climbs up the hill, then switchbacks right to head back toward the bank of Deep Creek. The trail then contours north, staying well above the creek for a while before dropping down to cross it at a place where it is open and there is some visible flood damage.
Cross the creek to the east side and continue north watching for cairns in the generally open terrain. The trail follows some rivulets coming down from the mountainside which probably represent the stream that shows on the map that flows off the western flank of Ruffner Mtn. After crossing these rivulets, the trail angles northeast and ascends through another forested area and a nice glade of low aspen. It emerges into another meadow area where two large cairns right across from each other and another cairn farther away indicate where the trail will climb steeply up the hillside and then into a deeply forested section, east of and well above Deep Creek by more than 100 feet. Continue up and stay away from the slope down to the creek. The trail gets a little sketchy in here, but just keep pressing on north and you will emerge from the forest and walk down toward the side creek coming in from the east that drains the basin between the west flank/ridge of Ruffner and the west ridge of S8. A cairn marks the crossing point of this creek. This area marks the end of the main trees in this valley. From here, you can either begin an ascent of S8 by going up the steep, grassy slope and ridge ahead, or you can continue on up the main drainage. The trail plays out or degenerates into a multitude of domestic sheep trails that climb uphill through tall grass.
For the west ridge, hike up a moderately steep and grassy slope, passing through a small, rocky cliffband and work your way up on much steeper slopes toward the ridge, finally gaining it well along in elevation. The higher you hike, the more the ground cover deteriorates from grass and tundra to small, loose rock. Footing becomes increasingly difficult. The steepness of the ridge does not lessen for some time and you will continue to struggle until reaching the summit.
If you continue into the upper basin for access to S9, you will pass a nice grove of last trees and turn eastward toward another basin that lies west of and between S.8 and S.9. Take your pick as to which peak to ascend. We offer this warning: an ascent from here of either summit (S8 or S9) will involve a very difficult hike up small, loose scree of more than 1,000 feet in elevation. This is the kind of stuff that's "two-steps-forward, one-step back." We recommend going up the grassy slope mentioned before to the S.8 west ridge, but even this ridge is comprised of similar stuff. The view from this summit of the peaks to the east and the sheer cliffs and rocky faces is quite spectacular.
From S.8, return as you came or continue to S.9.