This loop can be done in either direction, though we recommend starting on the eastern side—the Sheridan Crosscut trail—and hiking counter-clockwise, due to potential difficulties route finding traveling the other direction. Either way, bring a topo map and knowledge of how to read it, as the route can be notoriously difficult to follow at the top.
From the Sheridan Crosscut “trailhead” roughly a mile up Tomboy Road, be prepared to climb steeply for the next two miles. The trail is narrow and occasionally overgrown, resembling a goat path more than an established trail in many places. There are very few switchbacks—you’ll mostly just go straight up the mountainside. As you climb, the views grow more and more awe-inspiring. Enjoy, especially, the front-row seat to Bear Creek Canyon across the valley, with its rushing waterfalls and jagged cliffs. A few brief goat-trail spurs here and there lead to especially impressive vistas overlooking the entire Telluride valley.
After scrambling up an especially steep slope around a sizable boulder, the trail disappears into an open meadow. From here on up, just follow the ridgeline steeply for another half-mile or so until you hit a clear trail on your left. Take this to traverse the mountainside into a stunning open basin beneath Mendota Peak and St. Sophia Ridge—and, from there, begin your descent through the woods on the Liberty Bell trail.
On your way down—for the most part, a scree-laden wide path, with some smooth stretches here and there—don’t miss the old mining ruins and debris. After a relentlessly steep descent, you’ll pop out into a glorious meadow of aspens before hanging a left on the Jud Wiebe Trail for the quickest route back to Tomboy Road or town.
Keep in mind: particularly on the Sheridan Crosscut side, the trail is open and exposed, so wear plenty of sun protection. There’s also very little water along the way; pack plenty of your own. Start early in the day to avoid being caught on high, open slopes or ridges in an afternoon thunderstorm.
What Makes It Great
Few people know about the Sheridan Crosscut Trail, and because it is as steep and burly as they come, you’re likely to have it—along with its breathtakingly gorgeous panoramic views of the surrounding mountains—largely to yourself. The Sheridan Crosscut trail lies on a sunny, open, east-facing ridge, so it’s also one of the fastest high-alpine trails to melt out in the spring.
Who is Going to Love It
Adventurous souls seeking solitude, some navigational exploration, epic 360-degree views, and a calf-quad-and-glute-crushing challenge.
Directions, Parking, & Regulations
There is no trailhead sign for Sheridan Crosscut. Start at the base of Tomboy Road (north end of Oak Street) and hike or drive (high-clearance vehicles only) to the second major switchback in the road. Shortly past it, look for a faint, steep swath of singletrack on your left-hand side, marked with a large, gnarly tree stump popping out from the ground diagonally. This is your trailhead!
A few parking spots are available at pullouts or switchbacks along Tomboy Road, though we recommend just parking in town and hiking up to the trailhead. Note: many streets in Telluride are limited to two-hour parking, so be wary of these restrictions—or seek free, all-day parking at the Carhenge Lot on the southwest corner of town, off West Pacific Ave.