Driftless Dagger 2025

The Driftless Dagger is a self-supported bikepacking race through one of the Midwest’s most challenging and geologically unique landscapes. Spanning Illinois, Iowa, Minnesota, and Wisconsin, it takes riders deep into the Driftless Region—an ancient land of rugged valleys, steep ridges, and scenic bluffs overlooking the mighty Mississippi River. Riders can choose between two routes: the 550-mile Dagger with 38,000 feet of elevation gain or the 237-mile Baby Dagger with 18,000 feet of climbing. Both routes begin and end at Chestnut Mountain Resort in Galena, IL, two hours west of Chicago.

Unlike the flat plains that define much of the Midwest, the Driftless Region was never flattened by glaciers, leaving behind a labyrinth of undulations and relentless climbs that will feel like death from a thousand cuts. Riders will experience 70% unpaved surfaces on the Dagger and 60% on the Baby Dagger, encountering quiet gravel roads, hidden backcountry stretches, and punchy elevation gains that add up fast. Small towns provide intermittent resupply, but remote sections demand careful planning.

More than just a race, the Driftless Dagger is a ride through history—a journey across landscapes untouched by time, where every climb and descent tells a story millions of years in the making.

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