It it easy to underestimate this challenging little trail leading to the Tilly Jane A-Frame. Because the trail is only 2.5 miles one-way, a little extra weight from gear, food, or drinks that may make your overnight stay a little more luxurious might seem acceptable. Keep in mind, however, that the trail climbs 1,9250 feet in those 2.5 miles. The hike can feel like an unforgiving slog with a heavy pack.
The trail is beautiful, however, and worth exploring even if you haven't been fortunate enough to land an overnight reservation at Tilly Jane or at the Guard Station. The early portion climbs through ponderosa and lodgepole pine, white fir, western larch, and mountain hemlock. One-third of the way up, however, the views open up as the trail enters the burn area from 2008's Gnarl Ridge wildfire. On a clear day you will enjoy constant views of Mount Hood's north face, Mount St. Helens, Mount Adams, and Mount Rainier.
Naturally, the steep climb in also means a steep descent out. The Tilly Jane Trail may not be the best choice for cross-country or backcountry skiers leaving the area; fortunately, descending the nine miles on Cloud Cap Road is an excellent option. The road offers plenty of shortcuts for those eager to return quickly and a gradual, graded downhill for those who remain on the road. The views are spectacular, as well.
Winter backcountry adventures can be dangerous outdoor activities that pose significant risks as conditions affecting safety (i.e. weather, snowpack stability, avalanche hazard) are constantly changing. Prior to engaging in these activities each individual should get the proper training to make safe decisions and be equipped to use avalanche safety resources and tools. Please visit our Backcountry Skiing and Avalanche Safety post to learn more.