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 past the Dauntless Mine (Photo #2) and up the road to 12,500’ where there’s a road junction. An alternate route up Sheridan starts off to the left - see description below. For the standard trail, turn right at the junction and continue 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 Sheridan-Sherman saddle - Photo #8. Follow the cairned trail up to the west - Photo #9. In winter/spring, you may have to carefully navigate past a cornice along the ridge. From the 13,150-foot saddle, Mt. Sherman is to the right and Sheridan is to the left (south). Taken from the side of Mt. Sherman, Photo #10 provides an overview of the saddle.
Turn left and hike south along the saddle or follow a trail that bypasses the higher terrain of the saddle on the west side - Photo #11. Walk 1/4 mile to reach the Sheridan side of the saddle (Photo #12), near 13,200’. Follow a trail up Sheridan’s northeast ridge - Photo #13. The trail stays just right of the ridge crest and is easy to follow - Photo #14. Just below the summit, the trail swings left (southeast) before climbing directly up toward the summit - Photo #15. Photo #16 looks west across the summit. Taken from White Ridge, Photo #17 is a different look at the route and also shows the alternate/shortcut described below.
Anternate Route: Shown as a dotted-line in Photo #17, there’s a shortcut that can be used when the terrain is free of snow. From the road junction near 12,500’, stay left on an old section of road that continues directly west - seen in Photo #3. Follow it to a mining area at 12,800’ and turn left to find an old trail that climbs south up Sheridan’s rocky east slopes. Carefully follow this old trail to reach easier terrain above 13,000’. Follow trail segments up Sheridan’s east slopes to reach the summit.
Most skiers drop off Sheridan’s south/southeast ridge (Photo #20 and Photo #21) and ski the east slopes back to the road.
Many people climb Sheridan in combination with 14er Mt. Sherman. By climbing this route to the Sheridan-Sherman saddle, you can climb the peaks in either order and descend to the saddle, past the Hilltop Mine and down the road.