From Hessie Trailhead, fork left when you meet Fourth of July Road. When the road becomes water, take the trail on the right and begin walking across boardwalk lumber beside the river. This continues for about 200 yards until you’ll reach a dirt parking area, presumably empty due to impassable water. This is the proper Hessie Trailhead and Hessie Townsite. Follow the rocky dirt road past some historic cabins. These are private property. Shortly after the cabins you’ll cross a bridge, the first of the day.
Beyond the bridge, the dirt road will start to wind upwards where is dissolves into single track. At about mile 1.3 you’ll reach Jasper Creek. To complete the trail in a CCW direction, do not cross the bridge, but take the trail on the right immediately before the bridge. Signs point toward Devil’s Thumb. From here, you’ll cross numerous water trickles along the trail the whole way to the Continental Divide. Near mile 4.8, You’ll reach Jasper Lake, a great spot to filter water. Continue to follow signs for Devil’s Lake and High Lonesome Loop. There are short spur trails near Jasper Lake that lead to campgrounds.
At treeline, approximately 11,100ft and 5.8 miles in, you’ll reach Devil’s Lake. Water is typically plentiful in this area. The Continental Divide lies in front of you, with 700ft of steep climbing to crest the ridge. It is worth noting that early season travel here can be potentially dangerous with large cornices and steep snow at the top of the ridge, and across the Continental Divide in general. Proceed within your abilities and with extreme care when snow is present.
When you crest the ridge onto the Continental Divide, the trail dissipates and is almost non existent for the first hundred feet. Do not follow parallel to the cliffs, but, head southwest toward Winter Park, dropping about 100ft in elevation before finding the trail again. The trail is narrow, but can be easily followed. In about 2.2 miles, near mile 9, you’ll see Rollin’s pass ahead of you, and King’s Lake directly over your left shoulder. A junction with numerous signs awaits. Drop left, paralleling the shoreline of King’s Lake. If you pass Rollin’s Pass, a 4×4 road, you have gone too far.
After dropping off the divide and passing King’s Lake, the trail follows a mostly straight line through the pines. Near mile 13.5, a large wooded sign, “Indian Peaks Wilderness” will be on your right. Continue forward, where you’ll encounter a large field and a sign on the left. Do not cross the field, but, fork right, crossing a bridge and the stream. The trail gets noticeably wider from here before dropping a steep hill. At the bottom of this hill, you’ll be back to the bridge where you had previously split right toward Devil’s Thumb. As you cross the bridge, fork right, following the wide trail in the direction of Hessie Trailhead, back to where you started.