Triple D Endurance Race

The quirky aspect of the Triple D Winter Race is that you never quite know what you’re signing up for. Some years, racers pedal or run over firm snow or frozen ground under bright blue skies. Other years, they slog through snow, slush, mud, and cold so biting it fogs your thoughts. Either way, when you line up on race morning in mid-January, you know you’re in for an adventure! Named after the eastern Iowa communities that portions of the race either start at or pass through - Dubuque, Durango, and Dyersville - this winter’s edition takes place Saturday, January 17, 2026.

Beginnings and Current Race Options

While some assume Triple D began as a bike race, event director Mark Stender clarifies its origins. “It started as run, bike, and cross-country ski races in January 2008,” he says. “We generally don’t have enough reliable snow to plan for skiing anymore, but the biking and running events continue.” From those beginnings, Triple D now features a full menu of cycling and running options:

For 2026, Stender says the start and finish locations remain the same, keeping the race’s signature routes intact. Cycling events start from the 7 Hills Brewing Event Center in Dubuque, and the running races start along the Heritage Trail in the tiny village of Durango. “We’re bringing back the 17-ish mile Half Double D as a race for a taste of Triple D,” he says. “All the other distances are the same as last year.” There’s also a Poker Tour option for the Half Double D 17-mile distance, so if you don’t want to race it, you can choose this non-competitive ride that invites participants to take in the route, collect cards along the way, and trade stories at the after-party.

The Triple D’s running events and portions of the bike events take place on the Heritage Trail, a former 26-mile railroad line between Dyersville and Dubuque that was converted into a multi-use recreational trail in the 1980s. The Iowa Natural Heritage Foundation played a crucial role in converting this area to a crushed limestone trail, now popular for hiking, biking, and other activities, offering scenic views of rugged woodlands and the Little Maquoketa River.

The Author’s Takeaway

I raced the Triple D on my fat bike in 2023 (the 35-mile Double D option), and conditions that year leaned toward the forgiving side. Temperatures were relatively mild, and only a few areas of snow remained in shady spots. What struck me most was the variety of terrain. The route wove through everything from paved and gravel roads, crushed limestone trails, winding woodland paths, and across snowmobile trails and farm fields. The lack of snow certainly didn’t mean a lack of challenge! Cruising through farm fields without snow cover, the snapping sounds of riding over soybean stubble that day made me wonder if even my burly fat bike tires were going to make it through the race unscathed! There’s also some solid elevation gain in the bike races, and by the time I reached the aid station at the top of Sundown Mountain (a local ski resort), I understood why it’s one of the most celebrated points of the race. Reaching the summit feels like a small triumph. Inside the ski lodge, volunteers greet you with hot food, drinks, and smiles; the kind of Midwest hospitality that - along with catching up with fellow riders taking a break - makes you linger a little longer than you probably should. The mix of surfaces and scenery on the Triple D kept it fresh throughout the race, reminding me that this isn’t a typical Midwest bike event.

From Mild to Wild

If there’s one constant at Triple D, it’s unpredictability. While Midwest winters may see some mild stretches in mid-January (such as the one that greeted me at the 2023 event), that certainly was not the case in the 2024 edition of the Triple D.

“Snowpocalypse two years ago was one for the books,” Stender recalls. “We had a foot of snow on Tuesday and Friday before the race. There were only a couple of finishers in the 35-mile Double D, and none for the 70-mile Triple D.”

That same year, Michael Maney, a multi-time winner of the fat-bike division, faced one of the hardest days he’s ever had on a bike. Maney went into it knowing that a lot of fresh, deep snow was in store and conditions might be brutal. “I had the right mindset going in that it was going to be a long, hard day, and I definitely got my money’s worth!  It took us around five hours to get to the first aid station - 20 miles in,” he says. “Conditions were largely unrideable and we hiked our bikes for long stretches of an 18-mile section.”. At Sundown, the lure of hot pizza and Toppling Goliath’s Pseudo Sue proved too good to resist. “We knew we weren’t making it all the way to Dyersville,” Maney admits. “But after waiting out the afternoon, the snow firmed up considerably, and we were able to ride on the snowmobile trails with low pressure in the tires. I rolled in smiling as the second (and last) finisher of the 35-mile course that day. That one will be memorable for a long time!”

His story captures the essence of the race: conditions may humble you, but they also forge camaraderie and resilience. Sometimes it’s not just about beating others; it’s about surviving the day.

Racing on Snow and Ice: A Different Animal

Maney loves the unique rhythm of winter cycling. “Racing on snow and ice rewards having finesse and being smooth with your inputs to the bike,” he explains. “It takes time and focus to excel, but I love the challenge and growth that comes with it.”

He points out how traction and resistance constantly change. “Compared to dirt or pavement, traction is less predictable. Pedaling through deep snow drags your speed down even when you’re putting out the same effort,” he says. “Having a growth mindset is key. And a good set of studded tires or deep-lugged snow tires helps too.”

His comments resonate with anyone who’s spent hours on a fat bike in uncertain conditions. It’s equal parts strategy, endurance, and patience. Sometimes you’re riding. Sometimes you’re hiking. Sometimes, you question your life choices. And sometimes - especially when the snow crunches just right - you’re grinning ear to ear, reminded of why you signed up.

How to Survive (and Enjoy) Triple D

Maney’s advice for preparation is practical: train smart, layer right, and respect the elements.

Training: Mix structured intervals indoors with outdoor rides on the fat bike to adapt to the terrain.

 Gear: Dress in layers—windproof shell, insulating middle layer, and synthetic or wool moisture-wicking base. Use pogies to keep your hands warm and stash snacks within easy reach.

 Footwear: Waterproof winter boots are recommended, with chemical toe warmers for backup in extremely cold weather.

Lighting: Always bring a good headlight and taillight, especially if there’s any chance you won’t beat the sunset; daylight fades quickly in January.

 Nutrition: Bring more calories than you think you’ll need. The cold burns energy at a surprising rate.

For hydration in frigid temperatures, Maney’s strategy for success includes using insulated bottles filled with near-boiling hot water and keeping one of those bottles in a jersey pocket on his back, inside his jacket to help prevent freezing. “It’s not fun being without liquid water for a few hours between aid stations if conditions are really frigid. In the most extreme conditions, vacuum-sealed insulated coffee mugs can be a savior”.

Triple D rewards those who respect its unpredictability, as Maney puts it, “You never know what might slow you down out there. And don’t underestimate how much more energy your body burns in the cold.” He encourages those with questions or who may want more details about the event or preparing for winter riding to reach out to him at maney@uwalumni.com.

A Race with a Purpose

Beyond the miles, snow, and mud, Triple D is about giving back. Proceeds from the race benefit TMBR (Tri-State Mountain Bike Riders), a nonprofit organization that builds, maintains, and promotes local trail systems and mountain biking throughout the Dubuque area. “The event is a fundraiser for TMBR,” Stender says. “The proceeds go toward maintaining the trail systems they support. So be brave and sign up - one thing we can almost guarantee is you’ll have stories to tell.”

Whether you’re a runner chasing your first winter marathon or a cyclist testing your limits on a fat bike, you’ll find the Triple D’s combination of challenge and community hard to beat.