Driftless Dagger 2026

The Driftless Dagger begins and ends in Galena, Illinois, sending bikepackers into the steep Driftless Region for a nonstop ride. The primary Dagger route covers 550 miles, with a shorter option offered, and the listed Grand Depart is scheduled for early October. Participants may enter solo or in pairs, with the race emphasizing continuous movement over staged riding. The course has its warning, "death by a thousand cuts": not one massive climb, but a relentless succession of hills in a region that offers no respite. Twelve riders participated in the inaugural edition, and the event is growing into a full weekend. A notable tradition is a $10,000 charity prize; the first Dagger-distance finisher completing the course in under 42 hours, averaging approximately 13 mph elapsed, may designate a non-political, non-religious 501(c)(3) organization to receive the donation.