Prepare for an unforgettable challenge at the Dairyland Dare, Wisconsin's oldest gran fondo, set to unfold on August 1st, 2026, in the scenic hills of Dodgeville, WI. This acclaimed event draws participants to the unique Driftless Area of southwest Wisconsin, a landscape untouched by glacial flattening and renowned for its intense hills, steep forested ridges, and deeply carved river valleys. Riders can choose their adventure from demanding distances of 50K, 100K, 150K, or the epic 200K, tackling some of the Midwest's most formidable climbs.
The Dairyland Dare course promises breathtaking scenery as you navigate through the historic streets of Mineral Point and across the picturesque countryside of Iowa County. Participants consistently praise the event for its exceptional organization, top-notch support, and a truly beautiful route. Aid stations are legendary, fully stocked with an abundance of food and sports drinks, while dedicated community volunteers provide unmatched encouragement. On-course support, including mechanical assistance at key rest stops and roaming SAG vehicles, ensures a well-supported journey from start to finish.
With typical race day conditions in early August seeing highs around 82°F and lows near 61°F, alongside a 16% chance of precipitation, be ready for a dynamic ride. The Dairyland Dare culminates in a lively post-ride celebration, offering music, laughs, and a hearty meal to refuel and commemorate your achievement. Whether you're aiming for a personal best on the challenging climbs or simply seeking a spectacular ride through stunning terrain, the Dairyland Dare offers an unparalleled experience.
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