(WINTER) HOLD ON! If you don't have much high-elevation, winter climbing experience, be careful in your planning and take a partner. Even the "easy" 14ers (Quandary, Sherman, Grays & Torreys) can be deadly in winter.
From Fairplay, drive just over a mile south on U.S. 285 and turn right onto County Road 18. Drive 10 miles to a large parking area at 11,250'. This is the Leavick site. There is a large mine building on the right before the parking area. The road starts to get rough after this point but passenger cars can slowly drive another 1.5 miles before the road gets harsh. There are a couple of small pull-offs between 11,700' and 11,900' and more parking before a gate near 12,000'. The gate is usually closed. In winter, the road is usually plowed only to 11,100' which is one mile below the Leavick site.
From your parking spot, hike up the road and pass the gate at 12,000' - Photo #1. Continue to the Dauntless Mine at 12,300' (Photo #2) where there are several mine buildings near the road. At 12,500', turn right at a road junction and stay on the main road - Photo #3. Walk east and then north as the road crosses a large flat area (Photo #4) below the Hilltop Mine. Follow the road north (Photo #5) to traverse the slope under the mine and, at 12,800', turn back to the left (Photo #6) as you approach the upper mine area.
Continue on the road across a flat area to a point just west of the main Hilltop Mine building. The saddle between Mt. Sheridan and Mt. Sherman is up to the right (west) - Photo #7. Stay on the road as it passes a pile of gray rock. Shortly after this point, look for a cairn and trail that heads toward the slope below the saddle - Photo #8. Follow the cairned trail up to the west. In spring, you may have to carefully navigate past a cornice along the ridge. From the 13,150-foot saddle, turn right to see Sherman's Southwest Ridge - Photo #9.
The start of the ridge appears to have many trail options but there are really two defined trails that can be used to climb the initial bump on the ridge - Photo #9. Above 13,400', the ridge narrows and the trail approaches the more-defined ridge crest - Photo #10. Near 13,600', reach a small notch in the ridge (Photo #11) and continue along the ridge crest. The remaining hike quickly comes into view (Photo #12) as you reach the most difficult portion of the hike - a narrowing ridge with somewhat loose rock - Photo #13. Continue to the final pitch below the summit ridge (Photo #14) to find some confusing trail options. Stay near the ridge crest and ascend to the south end of the long summit ridge - Photo #15. Walk less than 0.25 mile to reach the true summit - Photo #16. Taken near 13,800', Photo #17 is a look down at much of the route.
When dry, the road can be driven to 11,800' by most passenger cars, with good clearance.