Singletrack/MTB
Gravel/All-road
Dirt-road Touring
Fat-bike
Twelve riders lined up for the inaugural Driftless Dagger event, tackling either a 550 or 237-mile bikepacking race through the Driftless Region of Illinois, Iowa, Minnesota, and Wisconsin. Find a recap and photos from the organizers here…
Words by Jack Peck, photos by Jack Peck and Cody Schlabaugh
The inaugural Driftless Dagger rolled out from Galena, Illinois, on September 20th, 2025, with a 7:00 a.m. start at Chestnut Mountain Resort. Two self-supported routes introduced riders to the rugged Driftless Region: the 550-mile Dagger with 40,000 feet of climbing (30% pavement, 70% unpaved) and the shorter but no less punishing 237-mile Baby Dagger, packing in 20,000 feet of climbing on a 40/60 split.
A Small but Spirited Field
As with many first editions, the numbers were modest, but the energy was high. Two riders toed the line for the Dagger, with representation from Colorado and Wisconsin. Only one would finish. Ten lined up for the Baby Dagger, traveling from Illinois, Iowa, Oklahoma, and Louisiana. For several, it was their first time at a bikepacking-style race, and for some, their longest ride ever. Sarah Rice, who raced Mishigami earlier this summer, made a last-minute call to enter, deciding just 12 hours before the grand depart.
The Course and Conditions
The Driftless has a way of speaking for itself. Endless rollers, steep B-roads, and punishing gradients piled on the difficulty, while big-sky views rewarded the effort. Forecasts hinted at rain, but riders got away with only a few sprinkles. Mud never materialized, and no route changes were required. For most, the challenge was stringing together climb after climb, cut after cut.
Baby Dagger Storylines
The Baby Dagger lit up early when John Whipple pushed to the front from the gun and never looked back. He sealed the win in 17 hours and 23 minutes.
Tire choice quickly emerged as a storyline: some riders rolled out on 38mm gravel tires, while others opted for 2-inch rubber. With the first half of the route being relatively tame, narrower setups initially looked efficient, but once the roads grew rougher past the halfway point, the bigger tires proved more forgiving.
Behind Whipple, Jacob Spath and Sean Ragee-Nelson traded places before finishing within 80 minutes of each other. Hot on their heels was Sarah Rice, the first female finisher, arriving just one minute behind Ragee-Nelson. Many riders described the experience as one of the hardest, yet most rewarding rides they’d ever attempted.
“Thanks again for putting the race on. It’s a real gift to the cycling community,” Whipple said. “The course is so awesome, I wouldn’t change a thing. I hope the Dagger becomes a marquee grassroots ultra.”
The Long Cut
On the 550-mile route, Zach Cole scratched around mile 100, leaving Andy Boone of Viroqua, Wisconsin, as the lone rider. Racing single speed, he pushed through on minimal rest—less than three hours total—and crossed the line after 2 days, 10 hours, and 40 minutes.
His effort not only secured the win but set a high bar for future editions. Along the way, he overcame a puncture that forced him to tube his rear tire at mile 365, right before one of the rowdiest descents on the course. “Really fun route… till I hit your Galena section. Then you were dead to me,” Boone joked. “There are some hard sections in there…I don’t know how you found some of those roads.” Boone’s ride highlighted the essence of the Driftless: beauty wrapped in brutality, terrain that humbles riders as much as it inspires them.
Scratches and Anecdotes
Three Baby Dagger riders failed to finish, citing illness, fatigue, or mechanicals. Still, most pulled the plug with smiles, already plotting a return. Riders had to deal with waist-high weeds on minimum maintenance roads, bovine, and comically steep hills throughout the route. For many, the hardships were matched by a rare sense of accomplishment. “Besides the angry cows and the waist-high weeds we had to hike through, I loved the course,” Spath said. “I haven’t had this sort of accomplishment from many other rides,” added William Boyle.
A Community Effort
The start and finish at Chestnut Mountain Resort made for a fitting backdrop, with big views of the Mississippi River and lift-served MTB trails that might make their way into next year’s route. Race director Jack Peck credited Luke at Chestnut, James Hillis in Jo Daviess County, and Zeno Molteni—described as a “route-making connoisseur”—for helping shape the course. A charity challenge added intrigue: $5,000 pledged for a Baby Dagger rider averaging 18mph and $10,000 for a Dagger rider at 16mph. No one met the ambitious marks this year, but they remain tempting goals for future editions.
Looking Ahead
The Driftless Dagger’s first edition embodied what grassroots bikepacking is all about: a small group of riders taking on a big landscape, fueled by curiosity, grit, and community support. As Boone put it after his finish, the Driftless doesn’t give you anything for free. And that, perhaps, is what makes it worth coming back to.
More info can be found at: Official Route Collection, Live Tracker Archive, Midwest Ultra Cycling / Dagger Website, @driftlessdagger on Instagram, Midwest Ultra Cycling YouTube.
Further Reading
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