Before the end of my trip, I ask Caldwell why he has embraced the Fortress and what he thinks of the future here. He reiterates the energy and motivation it takes to hike up here, establish a line — usually from the ground up, since the walls are too tall and steep for rapping in — and succeed on a hard project. Yet amid the general laziness that can surround sport-climbing development, he sees an encouraging new trend, that more and more people are getting tired of the same old thing. They are looking for something new, and are willing to work for it. For Caldwell, the investment pays off. “I love coming up here because I feel like I need a project to be living my life to the fullest,” he says. “I will always have projects here.”
Given the astronomical standards that Caldwell and others already have established at this cliff, I hesitate to press him about what one of these projects might be, but my curiosity gets the best of me. His answer is perhaps as predictable as it is inspiring — the extension to Kryptonite. “It would be cool to have something that went to the top of the cliff,” he says. “It’s got to be at least a 300-foot pitch.” When I ask when, he pauses. Silence. Finally he offers, “It will be a little while.”

Tim Kemple’s photographs (and desperate New England headpoint ascents) appear regularly in the pages of Climbing. This is his first feature-writing project.