I use mountain metaphors with a regularity that long ago gave up any pretense of originality. Such allusions come naturally to a hiker, a striver, someone who values both the art of finding the route and exploits of physical skill, to the point that they become rote. They leech through my travel writing, my fiction, and my political advice. “We have other mountains to climb,” I tell a friend who, like me, has suffered a setback in what I have started to call a summer of disappointment. It has been a summer of deferred dreams and stalled-out ambitions, though any frustration is only the product of the lofty heights we have sought for ourselves. The pursuit alone is part of the allure, though after a view from higher up, the same old woods may not feel quite as satisfying.

My annual hiking trip with my uncle Bob, cousin Rob, and friends Amy and Ed takes me to the highest reaches of Colorado. It orbits around Leadville, the only settlement of over 1,000 people at an elevation over 10,000 feet in the United States, and to call Leadville colorful would only start to tell the story. An early silver rush turned it into the second-largest city in Colorado for a spell; even today, a healthy chunk of the world’s molybdenum comes out of the nearby Climax Molybdenum Mine. On the way up, this northern Minnesotan explains tailings basins to his fellow travelers and geeks out on this operation. Large parts of the town look rough, trailers and bedraggled bungalows along some streets that are practically sand, but at its core is some boom era architecture with lively hues, and an outbreak of new construction has created a ski town-style tumor on its northern edge. “Keep Leadville Shitty,” exhorts a local bumper sticker, a window into the battle for its soul now under way.

I am swiftly smitten by this city on an eternal frontier. Our arrival coincides with the closing stages of the Leadville Pack Burro race, the second leg of the pack burro racing triple crown and one of its most daunting courses. It is a magical spectacle. Every five minutes, the town police car circles back through to guide in another exhausting and sweaty human tugging on the rope of a burro, which may or may not have any interest in cooperating with the exercise. Onlookers cheer as the burros amble to the finish line by the booth from the Western Pack Burro Ass-ociation. One collapses into a chair next to us, his fifth 22-mile race complete, spent from the effort of coaxing his mighty steed across the line. The closed-down main street through Leadville hosts grand old architecture, placid burros willing to be petted, and t-shirts spanning the full gamut of ass puns. A week later, on our way out of the wilderness, cyclists for the Leadville 100 have replaced the burros, another reinvigoration for a small, rural town finding its late modern footing.

Our hike covers two segments of the Colorado Trail, a 485-mile path from Denver to Durango that takes its travelers through some of the nation’s most dramatic high country. We begin at the Tennessee Pass between Leadville and Vail and work our way south to a trailhead between Mount Massive and Mount Elbert, the state’s two highest peaks. Our campsites place us at the high-altitude Porcupine Lakes, an alpine meadow beyond Turquoise Lake, and among the wooded roots of Massive. With a tree line at 12,000 feet, the views from this part of the CT are not as stunning as last year’s jaunt on the Beaten Path, but the lodgepole pines provide pleasant hiking cover, and it takes little time for this group to settle into the rhythms of wilderness release.

As trails go, the CT itself is relatively benign. It is wide and well-maintained, sometimes with the feel of a hiking superhighway. On this stretch there is plenty of water, and resupply opportunities are abundant in nearby towns. There are just two great challenges to hiking the CT. The first is elevation, and with the entire hike happening above 10,000 feet, five flatlanders take some time in adjusting to the thin mountain air. Our first day is mercifully easy, but even then sleep comes terribly, and day two beats up the entire party, with me feeling about as gassed as I ever have on a trail after far-from-awful 400-foot climb midway through the day and fellow hikers collapsing in a grove at the bottom of the following 1,500-foot descent, all before the subsequent 1,000-foot march up to the alpine meadow where we make camp. A constant sense of dehydration looms over the trip, occasional lost appetites and bad sleep turning a routine hiking distance into a genuine chore.

The second looming threat throughout the week is the weather. Colorado has a short hiking season, and even now in midsummer, there is a chance that thunderstorms may roll in off the mountains every day. Early starts are necessary, lest the oncoming storms bear down while on some exposed stretch of trail. Our luck holds on the first three days, and though dime-sized hail does rain down on us high above the tree line on Mount Massive and lightning strikes behind the hulking peak, we make it back to camp without any ill effects and ride out the remainder of the lone storm to hit us. The wettest I got on the trip was on a hike from a restaurant to the hotel in Denver.

Mount Massive is the third-highest American peak outside of Alaska, standing shorter only than Mount Whitney and its immediate neighbor to the south, Mount Elbert. It also lives up to its name: while it may be 12 feet shorter than Elbert, it is far bulkier, a sprawling behemoth of false summits and lengthy approaches feeding up to one great ridge atop it all. We make camp for two nights at Willow Creek, which sits at 11,000 feet and cuts off six miles of the round-trip ascent from the nearest parking lot. The climb starts through the region’s characteristic pine forests, but in time the trees thin out into scrubby willows and then into rocky slopes studded with grasses and mosses. This stretch above the tree line is the longest part of the ascent, a steady march up and up through steadily choppier terrain. A saddle between South Massive and the main peak gives a stunning view down to mountain lakes and smaller mountains below, and a clamber takes the hiker up a ridge to a false summit and then on to the twin logs marking the point 14,427 feet above sea level.

Our group plods at a determined, if hardly speedy, pace. On the way down, we are promptly waylaid by a mountain goat, who takes his sweet time in vacating the path. Twenty feet onward, we encounter mama goat and baby. Baby plops down in the middle of the trail for a spell, and mama takes a leak on the path to further get the point across. By the time they finally move, the clouds are beginning to gather, and the goats provide further entertainment through a lunch stop back at the saddle. The Massive menagerie continues as we head down from there, as ptarmigans stroll past and a crew of marmots, some of them appearing rather obese, trundle about the slopes.

The human zoo on display on this trip, somehow, exceeds the variety of the wildlife. At the parking lot at the start, we get our picture taken by a British cyclist who began in Denver and is now working his way down to Mexico, an adventure that he expects will take him until March of next year. (Excepting the wilderness bits, which include the two segments we hike, the Colorado Trail welcomes cyclists.) When we roll into our camp for our first day, we come across two Missouri Mennonite newlyweds in traditional garb and their salt of the earth cowboy guide, riding horses up and down peaks for their honeymoon. One could mistake the image of the three of them for one taken in 1872. On that first night, we share the site with the Gu Girls, three through-hiking young women who have formed a trail family; on a resupply run in Leadville earlier that day, they chased down a truck distributing Gu, the energy gel for distance athletes, and they share some of their rather large haul with us. It all tastes awful.

We pass twenty Outward Bound kids for whom a 3-mile trek is torture, and later meet a teenage girl councilor for another group of OB boys who decides the route up Mount Massive, which she has just casually summitted in no time flat, will not do for them. A University of Florida biologist acclimates herself to hiking at elevation before she heads to Argentina, where she will work to preserve endangered chinchillas high in the Andes. We pick her brain on the diets of local rodents. Inevitably, we encounter a man wearing a shirt from the Bonfield Express, a now-defunct Thanksgiving 5K in Downers Grove, Illinois that Bob, Rob, and I often ran; this is the second straight year of a Bonfield moment of recognition a thousand miles from suburban Chicago, and we sing the praises of its shirts for hiking. Another Mt. Massive day hiker has just bagged his 27^th fourteener this year, while the two guys who summit just behind us crack beers together at the summit. No one, however, can top Nora, the 19-month-old through hiker. Her parents are carrying this intrepid traveler clear from Denver to Durango, each with 42-pound packs (Nora weight included), and report she is in good cheer after the first 185 miles.

The trip begins and ends in Denver, a city that inspires mixed feelings. The airport, a monument to 90s sprawl, is a contender for worst in the country, though Blucifer and the lizard people lair do liven things up. Its rapid growth is apparent everywhere, and at least the dense housing is going up in droves, albeit often in far-flung tracts of identical boxes. There is a charming district of craftsman bungalows south of downtown, and grand institutions like the capitol, Union Station, and a lush botanical garden give some status to the capital of the Mountain West. The food scene, with Rob as our guide through it, is solid, and of course I cannot complain about the beer. The American future on display in Denver is more comforting than that of other western American cities, freed from California world-saving hypocrisy or Vegas alternate reality or Phoenix total defiance of nature, but it remains choked by dust and ozone warnings and unattainable real estate, the sort of qualified success story that defines the nation’s epochal lurch. It’s a fun place to visit, but it isn’t home.

Shortly before this trip, I polished off David Brooks’ The Second Mountain, the columnist’s midlife crisis book in which he distinguishes between the mountain of earthly success and the mountain of moral formation that people can pursue in life. In my tension-obsessed way, I have made efforts to climb both peaks in the first third of my life, striving both for a home life worthy of an American Dream and a well-ordered life where I believe in what I do. At thirty-two, I find myself frustrated with my progress on both, in many ways proud of my progress but still clearly still gazing up at a false summit. I decide it is somehow fitting that my venture left the conquest of a second peak such as Mount Elbert for some future journey. We do, indeed, have other mountains to climb. But we are on a well-maintained path, and we have fellow hikers to go with us.