Death by a thousand cuts
Your choice: The Dagger with 550 miles, 38,000 feet of vert or the Baby Dagger with 237 miles, 18,000 feet of vert—both starting and finishing at Chestnut Mountain Resort in Galena, IL. This is where rugged gravel roads, steep ascents, and peaceful backcountry stretches meet the raw beauty of the Driftless Region. With minimal pavement, endless climbs, and small-town resupply stops sprinkled along the way it will feel like Death by a Thousand Cuts—a challenge built for riders who thrive off-road and live for big miles. Grand Depart: September 20, 2025. Are you ready to earn your scars?
Routes
Route Surface Estimates
Dagger: 30% paved, 70% unpaved
Baby Dagger: 40% paved, 60% unpaved
Rules
1. Complete the Course Under Your Own Power
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Stay on the prescribed route. If you leave, return to the exact spot you exited.
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Only detour for road closures or safety hazards
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No motorized assistance
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No drafting.
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For major mechanical issues, you may get outside help (excluding friends/family) but must resume from the breakdown point.
2. Ride Solo & Self-Supported
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You're responsible for yourself.
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No outside help unless it's commercially available to all.
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Carry your own gear—no sharing.
3. Equal Opportunity
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No pre-race caches or staged supplies.
4. Non-Stop Race
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The clock runs from the Grand Depart until you finish or scratch.
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No mandatory stops or rest periods.
5. Proof of Completion
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Use an approved GPS tracker with our event tracking service to verify your route and time.
6. Safety First
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Follow all traffic laws and ride safely.
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Wear a helmet at all times.
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Must have two headlights and two tail lights with separate power sources; lights on from dusk to dawn.
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Wear reflective gear when riding at night
7. Honor System
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Know the rules and self-police.
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Report rule violations within 48 hours post-race.
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Minor infractions may result in time penalties; major ones can lead to disqualification.
Driftless History
The Driftless Region is a geological anomaly—an ancient landscape untouched by the glaciers that flattened much of the surrounding Midwest during the last Ice Age. This left behind a rugged terrain of steep bluffs, deep river valleys, and winding ridgelines carved over millions of years by rivers like the Mississippi. The area’s name comes from the absence of “glacial drift,” the rock and sediment left behind by retreating ice sheets.
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The Mississippi River is the lifeblood of the Driftless Region and the focal point of both routes. Unlike the broad, slow-moving stretches seen farther south, the river here is dynamic—narrower, faster, and framed by towering limestone cliffs. This stretch of the Mississippi is a product of ancient forces, having cut through bedrock over millions of years to form the rugged topography that makes the Driftless so unique and the riding so challenging.
Ride Fast, Donate Cash
Elite racers who complete the course in the designated time will get to direct a donation to the charity of their choice!*
Time: 34 hours, 11 minutes
Speed: 16 mph avg (elapsed)
Donation: $10,000
Dagger
Time: 13 hours, 10 minutes
Speed: 18 mph avg (elapsed)
Donation: $5,000
Baby Dagger
*Restrictions apply. Donation award limited to the first place finisher of each event who completes the event in a total elapsed time with an average speed equal to or greater than the stated donation award thresholds. Routes are subject to change until the race begins. Times listed above are representative of the respective average speed. If route distances differ, average speed will dictate new target time to beat. Charity must be a registered 501(c)(3), not have political or religious affiliations, and is subject to approval by the Driftless Dagger race organizers. All race rules outlined above must be followed in order to qualify, including but not limited to following the exact designated route with GPS evidence via approved device.