Ride the Hills at Dairyland Dare
A Dodgeville challenge with big climbs, strong support, and a well-earned post-ride celebration.
Dairyland Dare returns August 1, 2026, inviting cyclists to take on the hills, valleys, and backroads of southwest Wisconsin. Based in the historic Mineral Point and Iowa County area, this Gran Fondo-style ride is known for scenic countryside, challenging terrain, and the kind of community support that helps riders keep going when the road tilts up again.
There are bike rides, and then there are rides you remember long after the last climb.
Set in Wisconsin’s Driftless Area, where the landscape was left untouched by glacial flattening, Dairyland Dare offers some of the most memorable cycling in the Midwest. Riders can expect quiet rural roads, steep forested ridges, deep river valleys, and climbs that reward every effort with sweeping views and a true sense of accomplishment.
With four distance options – 50K, 100K, 150K, and 200K – riders can choose the challenge that fits their goals. Whether you are building toward your first supported distance ride, chasing a big endurance milestone, or returning for another shot at the hills, there is a route waiting for you. Road bikes, tri-bikes, and e-bikes are welcome.
The ride is fully supported from start to finish. Participants receive a bib number, bike plate, helmet sticker, participant T-shirt, course map, and professional ride photos from Focal Flame. Riders will also have access to fully stocked aid stations, SAG vehicles, and on-site mechanical support throughout the day.
New for 2026, every rider will receive a Dairyland Dare Bike Ride collector’s patch to commemorate the day.
This year also brings an elevated post-ride experience with a fresh meal from Steve’s Tacos, a local food truck serving authentic, made-from-scratch dishes using locally sourced meats and fresh vegetables. Each rider can use their food ticket to choose any item from the Steve’s Tacos menu, while spectators can purchase meals and join the finish-line celebration. Riders will also receive two complimentary 3 Sheeps Brewing beers, music, and games at the post-ride party.
Riders taking on the 100K, 150K, and 200K routes will also enjoy a dedicated lunch rest stop featuring Steve’s Tacos’ specialty cold quesadilla, with or without protein, plus aid-station snacks and plenty of hydration to fuel the miles ahead.
Dairyland Dare is a day for riders who love a challenge, appreciate a beautiful route, and know that the best cycling events are about more than miles. They are about the roads, the people, the volunteers, the views, and the stories you bring home afterward.
Choose your distance, get ready for a day in the saddle, and come experience one of Wisconsin’s great cycling challenges.
Learn more and register at www.dairylanddare.com.
Bike Fed Supporters Receive a Special Registration Discount!
Dairyland Dare organizers are graciously offering a 25% registration discount to current Wisconsin Bike Fed supporters through 6am on August 1, 2026!
- Supporters who are eligible for the discount last received an email on June 24, 2026 with the exclusive code to enter during registration.
- Supporters who have not received an email communication with discount information, as well as new supporters who donate $50 or more, may contact the Donor Relations Team at donorservices@wisconsinbikefed.org or 414-626-1540 for questions and the codes.
Please note: discount codes may not be shared, transferred, or used to register others.