When Garry Kasparov, the world’s best living chess player, suffered a narrow defeat at the hands of IBM’s chess-playing computer Deep Blue in 1997, pundits around the globe opined that it was the final blow in the long-running conflict of man versus machine. There was only one problem with their commentaries: It was a battle that essentially never existed. If you scour history for examples of people trying to outperform machines, about all you’ll find is the tall tale of John Henry. In reality, the concept of man against machine has either been a philosophical issue, focusing on the dehumanizing aspects of technology, or the linchpin of sci-fi thrillers like The Terminator or The Matrix.

But that’s not the case in the small town of Durango, Colorado, where hundreds of cycling enthusiasts show up every May to test their strength, willpower, and endurance in the Iron Horse Bicycle Classic. They don’t make the journey to compete against each other, but against the relentless power of the machine that changed the course of history and the face of the American West: the locomotive.

You’d be hard-pressed to find a more appropriate setting than Durango for the Iron Horse Bicycle Classic, since the town might not even exist if it weren’t for a railroad. Founded in 1880 by the Denver and Rio Grande Railway, Durango became a terminus of the Durango & Silverton Narrow Gauge Railroad (D&SNGRR). Laid over the course of nine months in 1881–1882, the tracks between Durango and the mining boom town of Silverton were used to transport gold, silver, and other precious metals out of the San Juan Mountains. But the Panic of 1893 caused the collapse of the silver market and led to a slowdown in mining operations, and three years later two mines in Silverton tapped out. Over the next several decades, other events — government control of the line during World War I, the flu pandemic of 1918, more mine closings — forced the railroad to close temporarily.

But the 55 miles of track running through the mountains near the Animas River showcased some of the West’s most scenic vistas, and it proved to be the saving grace for both Durango and the D&SNGRR. Tourism replaced mining as the railroad’s raison d’être, and Hollywood’s discovery of the line’s panoramic views led to the railroad being featured in several films, most famously in the Oscar-winning Butch Cassidy and the Sundance Kid. Today, it’s estimated that more than 200,000 visitors ride the train annually.

Given that history, it’s understandable that most of the townspeople wouldn’t give a second thought to the sight of the steam-powered locomotive pulling out of town on its run to Silverton. But for Tom Mayer, the train was a bit more personal: It not only ran by his home, but his older brother Jim was also its brakeman. Add in Mayer’s passion for mountain biking and a little sibling rivalry, and before long the two cooked up an unusual bet: whether or not Tom could beat the train to Silverton on his bike. One day in 1971, as the train left Durango and passed the Mayer home, the whistle blew and Tom began pedaling his steel-framed ten-speed to Silverton in a race that would cover nearly 50 miles and over 5,700 feet of climbing. When the train pulled into Silverton, Jim found his younger brother waiting for him — and the Iron Horse Bicycle Classic was born.

The first official race was in 1972, and for 36 years cyclists have descended on Durango with one goal: to beat the train. The Iron Horse Bicycle Classic began as a professional event, but as it became apparent that top-flight cyclists were edging out the locomotive with little difficulty, a separate event for amateurs was added to the mix. Today, the Citizen Tour has eclipsed the 47-mile pro race in both participation and length. These “normal” riders, weekend warriors like me, line up at the Durango train station, ready to race against a circa 1925, coal-fired locomotive. Beating the train means pedaling for 50 grueling miles, a good chunk of it uphill, with no reward aside from a sense of satisfaction. Roughly 2,200 riders competed in the Citizen Tour in 2006, and in 2007 the organizers had to set the field limit at 2,500 to ensure the quality of the racing experience and to make the event more manageable for the local and state agencies who help run it. The event anchors a weekend-long festival that takes over Durango.

Past winners of the pro event include world, national, and Olympic legends like John Tomac, Ned Overend, and Juli Furtado. Such a lineage gives the Iron Horse a special mystique in the cycling world — and fuels the curiosity of amateurs like me. Soon after learning of the event, I began to wonder: Could I beat the train on such a tortuous climb? On paper, it seemed possible — but all my training is near sea level, while the Iron Horse route traverses two passes that are more than 10,000 feet above sea level. Then again, climbing is my strong suit…back and forth my mind raced, until I came to the realization that the question could be resolved only one way: by saddling up.

As I began my training regimen for the Iron Horse, I naturally became fascinated with the legend of John Henry, an icon of American folklore. The mythical Henry (some scholars say the tale is based on an actual person and real events) was a steel driver who hammered rail spikes (or chiseled blasting holes in rock — versions vary) for a railroad. When a newfangled steam-powered drill threatened to replace Henry and his crew, he challenged the machine to a duel. Armed with just a sledgehammer, muscle, and pure determination, he set out to prove he could work faster than the drill.

As my wife reminds me before the race, Henry did beat the drill — but died in the process. I wasn’t worried about sharing his fate, but there were some concerns, like sleet, snow, or freezing rain. Despite its Memorial Day setting, the running of the Iron Horse has been affected by blizzards several times. A 1995 snowfall forced some riders to turn around before reaching the finish line. Several riders suffering from hypothermia had to be rescued in 1996, and the next year the entire event was called off due to snow.

And even with perfect weather, there’s still the matter of the train. The locomotive averages over 14 mph (the trip from Durango to Silverton takes 3.5 hours), and in normal conditions I can easily average over 20. But “normal” includes neither oxygen deprivation, nor prolonged steep climbs of 3 and 6 miles, nor a finish nearly 2,800 feet higher than the start. Most rides start and end at the same place, with the speed lost on climbs offset by fast descents. But the Iron Horse is a one-way race. Standing at the start line on the flat valley floor and gazing at the towering peaks on the horizon, it looks like the one way it goes is straight up.

When the whistle blows, the excitement is palpable: My heart rate monitor shows a jump of 15 beats per second — and I haven’t begun pedaling. As more than a thousand cyclists roll out, the train pulls away slowly from the platform, then gathers momentum as the pistons pump faster and faster. Glancing at the train, I catch a glimpse of my wife at one of the windows, but I hardly notice the other cyclists. Though we’re all amateurs and are unclear about what lies ahead, doubt and worry are quickly replaced by sheer excitement. For the first half hour — a fast ride on flat roads closed to traffic — my face is transfixed in a broad grin. A singular thought has gripped me: This feels awesome!

The first climb is gradual. The next two are exercises in long, monotonous grinds in the lowest gears, separated by flat sections that are too short to get back up to top cruising speed. The threat of the train catching up spurs me on, and I think of Satchel Paige’s advice about not looking back “because something might be gaining on you.” I break that rule and see nothing but cyclists behind me. Soon I realize that the only thing missing in what has otherwise been a wonderful day is the visual presence of the train. Though the track parallels the road, it’s hidden in a deep valley or thick woods for the vast majority of the route. I’d imagined a final sprint against a chugging locomotive, but it wasn’t to be. In fact, racers crossing the finish line can’t even see the depot where the train comes to a stop: The riders’ finish line is now located a few blocks away from the depot.

The last climb over Molas Pass takes me to the highest elevation point of the race. Precious minutes tick away as I grind upward. Still, I feel good as I pass many Citizen riders — until I glance at my watch. As I reach the top of the pass and begin a short but fast descent into Silverton and on to a final sprint through town, it seems victory is slipping away. But no matter: I already feel like a winner because the ride was so epic and the weather and scenery so perfect.

Even though I’ve discovered I’m running 12 minutes behind the train’s pace, I expend my last bit of energy charging the line to finish like I started — grinning. Like all the other finishers, regardless of their time, I pick up my free “I beat the train!” T-shirt and am sufficiently moved to pay top dollar for a commemorative bike jersey.

When my wife finds me in the post-race celebration, I ask how long her train ride took. “Three hours and forty-two minutes,” she replies. It dawns on me: The Iron Horse also ran 12 minutes late. Due to a lack of witnesses, the Iron Horse and I will call this one a tie — with a rematch to follow.

WHEN YOU GO
Durango is a historic town with plenty of charm and endless activities — from boating and fishing on nearby Vallecito Lake to hiking and rock climbing in nearby Mesa Verde National Park. Restaurants, lodging, shopping, and performing arts abound. The biggest attraction is the scenic railroad, in full operation from May through October; reservations are recommended (durangotrain.com, durango.org).

The Iron Horse Bicycle Classic (ironhorsebicycleclassic.com) is held the Saturday of Memorial Day weekend every year. It’s now a weekend-long festival complete with a veloswap and post-ride block party and concert. A highlight is the “Cruiser Crit,” when locals in costumes race hilarious homemade bikes around downtown. Bike rentals are available, but you should book these as far in advance as possible — start with Hassle Free Sports (hasslefreesports.com).

Several hotels are on the edge of historic downtown, including the Doubletree Hotel Durango (doubletree.com) and Holiday Inn (holidayinn.com). On Main Ave., the Strater Hotel (strater.com) is a historic gem with Old West ambiance and a saloon where the staff dresses in period garb.

For such a relatively small town, Durango has an excellent bounty of dining options. For fine dining, the best choices are Ken & Sue’s (970.385.1810) and Seasons Rotisserie & Grill (970.382.9790). Zia Taqueria (970.247.3355) serves up great tacos, and check out Steamworks Brewery (970.259.9200) for casual fare and an outstanding beer selection.

Larry Olmsted writes from his home in Vermont.

Photography of riders by Sven Brunso/Durango Area Tourism Office.
Photo of D&SNGRR by Yvonne Lashmett.