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Dairyland Dare

Saturday, August 3, 2024 Dodgeville, WI 53533 US Directions


Dairyland Dare - 200K

$125 6:15AM CDT - 6:00PM CDT Price increases after July 31, 2024 at 11:59pm CDT

Dairyland Dare - 150K

$125 6:30AM CDT - 6:00PM CDT Price increases after July 31, 2024 at 11:59pm CDT

Dairyland Dare - 100K

$125 6:45AM CDT - 6:00PM CDT Price increases after July 31, 2024 at 11:59pm CDT

Dairyland Dare - 50K

$125 6:45AM CDT - 6:00PM CDT Price increases after July 31, 2024 at 11:59pm CDT

Ride Website

Additional ride information can be found at


Harris Park
600 N Bennett Rd
Dodgeville, WI US 53533


CLICK HERE for packet pick-up information.



Set in southwest Wisconsin, the land left untouched by glacial flattening during the last ice age, the Dairyland Dare offers some of the most extreme hills in the Midwest. The area is characterized by steep, forested ridges, and deeply carved river valleys.
Pick from 4 one day challenges: 50K, 100K, 150K, or 200K. We welcome road and tri-bikes alike. E-bikes are welcome as well, but must follow the timeline accordingly (Click here to view FAQ page.) Scheduled five weeks prior to Ironman WI, the Dairyland Dare makes a great, last long ride before starting your Ironman taper.
Riders will climb through the historic streets of Mineral Point, WI and across the scenic countryside of Iowa County (WI) along their quest to cover distances of 50km to 200km before the sun goes down. Many of Wisconsin's steepest climbs are located throughout this region. With an abundance of community volunteers, ride support is second to none. Rest stops are well staffed and very well stocked with more food and sport drink than you could possibly consume. On course support is ever present and mechanical support is provided at every rest stop.
Afterwards join us at the post-ride party and enjoy music, laughs, and a meal that won’t leave you hungry! Register early to guarantee a spot in this great ride!


  • Ride Bib
  • Bike Plate
  • Helmet Sticker
  • Professional Ride Photos
  • Participant T-Shirt
  • Map & Instructions
  • Experienced Mechanics on site and on course
  • SAG vehicles roaming the course
  • Fully Stocked Aid Stations - you won't go hungry!
  • Post Ride Party - including a well-deserved meal, drinks, and music!



Bib numbers, bike plates, wristband and helmet stickers must be visible throughout ride. Your bib number should be worn on the back of your jersey. This is so ride officials know who is part of the event and can ID you in an emergency. Failure to wear these items may keep you from getting any support from rest stops or SAG/mechanical support and could result in forfeiture of post-ride food/beer and/or future registrations.

Don’t be a bandit! This will not be tolerated. Anyone found to be an unregistered participant could face penalties up to and including prosecution. Both you and your friends will be banned from future events if you are riding with friends that are not registered.

Dairyland Dare is a bike ride, not a race. Please keep this in mind as you prepare. ALL TRAFFIC LAWS MUST BE FOLLOWED AT ALL TIMES. VIOLATORS WILL RISK BEING CITED AND/OR FINED. Please respect the residents and municipalities who have so graciously granted us the rights to ride through their communities. Plenty of resources are provided along the course. We will not tolerate violations of law. Acts of trespassing, public urination, disorderly conduct, etc., could lead to sanctions including an event participation ban and/or prosecution.



The Dairyland Dare, also previously known as the Wisconsin Dairyland Dare Cycling Challenge, was conceived and created by Stewart Schilling and Michelle Godez, avid cyclists from Southwest Wisconsin. The first ride took place in August 2006 and drew over 400 riders and offered three distances: 100K, 200K, and 300K. The ride doubled in size by 2007 and in 2008 two more distances were offered: 133K and 266K. By 2010 the ride grew to over 1000 riders and the distances that were offered expanded to: 50K, 100K, 150K, 200K, 250K, and 300K with very little overlap. This was the first year the ride included Mineral Point and Governor Dodge State Park. 2011 was the first year where Dairyland Dare was the final stage in the Wisconsin Triple Crown.

The ride embraced several themes over the years such as; the wild west; Dare Devil, paying homage to Evel Kneivel; Gran Fondo, with an early twentieth century Italian advertising; and an artistic theme from French Art Nouveau.

The event was purchased in 2015 by SyklusSport, LLC and held ownership until 2018. The ride did not take place in 2019 and was then purchased by Race Day Events. The event was cancelled in 2020 due to COVID-19. The distances now offered by the ride are 50K, 100K, 150K, and 200K.

Referral Program

Official Beer Sponsor

Post-Ride Refreshment Stand Sponsor

Waste Management Provider

Bike Techs

Valued Sponsors

Ride Contact Info

If you have any questions about this ride, click the button below.



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