Celestially, the longest day of the year happens around the third week of June, the summer solstice. If you’re a hiker, though, and you attempt to summit Mount of the Holy Cross via the Halo Route, the longest day of summer will begin the moment you leave the Fall Creek Trailhead at the top of Tigiwon Road. Five summers ago, for me and two fellow members of Vail Mountain Rescue Group on a busman’s holiday, that day was September 12. The time, if I recall, was around 5:30 a.m., and it was winter cold, pitch black.

We didn’t say much as we started up the trail, finding our rhythm as circles of light from our headlamps bounced along in the darkness. Together, we marched alone in our thoughts. My mind wandered to James Nelson, a 31-year-old hiker from Chicago who had set out on the morning of October 3, 2010, for a 25-mile solo trek through the heart of the Holy Cross Wilderness and inexplicably vanished. Two years later, hikers stumbled across some of James Nelson not far from his campsite off the Holy Cross Jeep Trail near Holy Cross City, an abandoned mining camp. In 2013, a mushroom hunter stumbled across more of James Nelson in that same area, and I was tasked to the VMRG recovery team that brought him home.

No doubt, Peggy and Scott, my teammates in front and behind me, were thinking about another Holy Cross casualty: Michelle Vanek, a mom from Lakewood who left the Fall Creek Trailhead at 6:30 a.m. on September 24, 2005, hiked the Halo Route (accidentally; she thought she was on the less-arduous standard route over Halfmoon Pass) and was last seen later that day, just below the Holy Cross summit, unable to make the final push to the top. Unlike Nelson, no trace of Vanek has ever been found.

Like Oregon’s Mount Hood (a relatively straightforward ascent requiring more chutzpah than technical mountaineering skill), Mount of the Holy Cross has earned a reputation as being an “easy” first summit and attracts thousands of peak baggers during the height of the summer season. On both mountains, people accustomed to day hiking in blue jeans and sneakers leave the trailhead equipped as such, toting little more than a disposable bottle of water and a cell phone for the requisite summit selfie. Halfway up, they discover that they’ve grossly underestimated the mountain; Holy Cross, like Hood, is the hiking equivalent of a marathon, not a fun run. To enjoy it, you had better be prepared to suffer.

With that in mind, I asked our backcountry correspondent, Devon O’Neil, to pen this issue’s cover story detailing routes not just to our fourteener’s summit, but also exploring the lesser-traveled trails of the much larger Holy Cross Wilderness, and how to experience it safely.

As a first responder accustomed to the backcountry, I thought I was ready for the Halo Route, and I was humbled. By lunchtime on Sept 12, we had reached the saddle of Notch Mountain, a satisfying endpoint for most. From there, the hard work to the summit began. For hours, we scrambled up and over boulders along a vertiginously exposed ridgeline, ascending and descending several 13,000-foot peaks. I remember standing atop Holy Cross at 3 p.m., then little more until we were back at our cars seven hours later. In the moment, that hike was a purgatory. As I recall now, it was heaven.