Driftless Dagger 2026

The 2026 edition of the Driftless Dagger rolls out on October 3rd at 7:00 AM from Chestnut Mountain Resort. This year, we’re joining forces with Lead Ore Gravel to create the Driftless Gravel Festival—a shared start line offering distances from 50 miles to 550 miles, all departing together into one of the Midwest’s most rugged and misunderstood landscapes.

Unlike the glaciated plains surrounding it, the Driftless Region was never flattened. What remains is a web of steep ridgelines, narrow valleys, and quiet gravel roads that demand patience and steady effort. The terrain isn’t defined by singular alpine passes but by accumulation—relentless rollers that stack elevation through the day and into the night. Small towns provide intermittent resupply, but long remote stretches reward planning and self-sufficiency.

A gravel bike with 45c tires is recommended across both routes. For the full Dagger, short-travel suspension is advantageous given the repeated hits of chunky B-roads, steep pitches, and long hours in the saddle, though it’s not required.

New for 2026, categories expand to include Pairs, Singlespeed, Para, and Athena/Clydesdale, reinforcing the event’s commitment to a broad and welcoming endurance community.

Driftless Dagger
Distance: 550 miles

Elevation: 40,000+ ft

Surface: ~70% unpaved

The full Dagger runs through Illinois, Iowa, Minnesota, and Wisconsin, linking remote gravel corridors across the Driftless Region. This is a fully self-supported event. Execution matters—pacing, fueling, navigation, and decision-making will determine the outcome more than any single climb.

Baby Dagger
Distance: 237 miles

Elevation: 20,000+ ft

Surface: ~60% unpaved

The Baby Dagger condenses the character of the full route into a tighter loop through the best of the Illinois and Iowa Driftless. The climbing remains consistent and deliberate, with many of the same ridgeline views and remote stretches—just in a more compact form.

It’s direct, challenging, and accessible without being softened. For many, it serves as an entry point to the region’s terrain; for others, it’s a fast and focused test of efficiency.

Registration: https://www.bikereg.com/dagger