Cycling Gravel via BikeReg

Driftless Dagger

Name: Driftless Dagger
Start: 2026-10-03T00:00:00Z

Galena, Illinois · Saturday, October 3, 2026

The Driftless Dagger is a cycling and gravel event held on Saturday, October 3, 2026. It is located at 8700 W Chestnut Mountain Rd in Galena, Illinois.

Date: Saturday, October 3, 2026 at 7:00 AM
Location: 8700 W Chestnut Mountain Rd
Galena, Illinois
61036
United States
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Links: midwestultracycling.com Register at bikereg.com

The Driftless Dagger is a self-supported bikepacking race through the rugged, untamed beauty of the Driftless Region. Choose between a grueling 550-mile route with over 40,000 feet of climbing or the Baby Dagger at 237 miles with 20,000 feet of vert. Starting and finishing at Chestnut Mountain Resort in Galena, IL, this race is Death by a Thousand Cuts—relentless gravel, brutal climbs, and peaceful back roads that challenge your limits.

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Oct

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Fri, Oct 02, 2026 at 6:00 PM

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Lead Ore Gravel

8700 W Chestnut Mountain Rd, Galena, Illinois, 61036, United States
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Distance: 0 m from Galena

Sat, Oct 03, 2026 at 7:30 AM

[Lead Ore Gravel_Logo_B.jpg]

Welcome to the 2026 Driftless Gravel Festival!

We have teamed up with the ultra distance race, the Driftless Dagger, to form a weekend long festival in the most underrated cycling destination the Midwest. The party will get started on Friday afternoon with shakeout rides, a kids race, and packet pick up. The festival will take place at Chestnut Mountain Resort which is located in the heart of Driftless country while also overlooking the Mighty Mississippi.

The Galena territory was founded by resilient, industrious folks who put the area on the map by being the first major site of the mineral rush in the United States. They mined over 21 million pounds of lead in just a 3 year period. If you want to finish The Lead Ore, you’ll need the same tenacity that these early pioneers demonstrated. The Lead Ore will take place from Chestnut Mountain Resort which is situated smack dab in the middle of the Illinois driftless region. This is arguably the most scenic region Illinois has to offer. If you have never been to the Galena area, you're in for a surprise. The area offers many activities for couples and families. We recommend making a weekend out of this one and taking in the full experience. There are no refunds or deferrals. BikeReg does offer registration insurance at checkout.

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CyclingGravelUltra via BikeReg
leadoregravel.com Register at bikereg.com
Oct

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Fall Fondo

301 E 5th St, Dubuque, Iowa, 52001, United States
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Distance: 29.5 km from Galena

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CyclingGran Fondo via BikeReg
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