(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.
Take US 24 through downtown Leadville to the southern end of town. Turn east onto Monroe Street and drive 0.2 miles. Turn right (south) on Lake County 2 (Toledo St). Follow CR 2 (paved) for approximately 3.8 miles to a fork in the road. Turn left on a 2WD dirt road and continue 3.0 miles up into Iowa Gulch to the trailhead. A total of 7 miles from US 24 in Leadville. The trailhead is unmarked - park along the road. If you're hiking Mts Sherman or Sheridan, locate the trail (below the edge of the road) as it heads toward the creek under the power lines.
In summer, you can drive all the way to the upper trailhead at 12,000', but in winter the Sherman road is closed at the intersection with County Road (CR) 2 - Photo #1. After leaving CR 2, continue 3 miles up the Sherman road to 12,000', below the mine buildings. Because this is an unmarked trailhead, the first priority is to locate the trail that leads across the basin. Find the small road that turns down and back to the right below the side of the main road - Photo #2. This is the best place to start. Walk down this road and look for the trail that starts on the left after about 50 yards. Photo #1 was taken on the main road looking down at the area. The trail drops down past a wooden electric pole and heads south toward the stream below. There are a few spots where the trail has been washed away. Stay with the trail as it weaves southeast through willows to reach the east end of Iowa Gulch. Continue south and southwest on the trail as it climbs up onto talus - Photo #3 and Photo #4. The trail becomes thin in some areas but it's fairly easy to follow. Continue to the gully that drops down between Mt. Sherman and Mt. Sheridan - Photo #2. The trail reaches the gully near 12,400' - Photo #5.
Stay on the trail as it climbs southeast along the left side of the gully - Photo #6. Your next goal is to reach the Sherman-Sheridan saddle at the top of the gully. The trail switchbacks up to 13,000' (Photo #7) before sweeping left to reach the north side of the Sherman-Sheridan saddle - Photo #8. Photo #9 was taken at 13,100' on the saddle and shows the remaining route.
Begin hiking north up Sherman's southwest ridge - Photo #10. There is a good trail all the way to the summit. You will encounter various trail sections but they all lead up the ridge. Between 13,600' and 13,800', the ridge narrows and there is only one trail - Photo #11. The trail will be on the ridge crest or slightly to one side. Photo #12 looks back down at the Sheridan-Sherman saddle. Follow the southwest ridge up to Sherman's long, flat summit - Photo #13 and Photo #14. Photo #15 looks down on Iowa Gulch and the trailhead.
At can be a bit difficult to locate the start of the trail from the main road. Look for a small road that starts off to the right. The trailhead is almost exactly at 12,000'.