Dairyland Dare Presented by Incredible Bank

Prepare for an unparalleled cycling adventure at the Dairyland Dare Presented by Incredible Bank, returning to Dodgeville, WI, on August 1, 2026. This prestigious gran fondo offers an formidable challenge across southwest Wisconsin's breathtaking, unglaciated terrain, renowned for delivering some of the Midwest's most intense hills. Riders can choose their test of endurance from 50K, 100K, 150K, or the demanding 200K distances, all winding through steep forested ridges, deep river valleys, and past the historic streets of Mineral Point and the scenic Iowa County countryside. Expect typical race day conditions with highs around 82F and lows near 61F, alongside a 16% chance of precipitation, making for a classic summer ride.

The Dairyland Dare has earned its reputation as Wisconsin's oldest gran fondo and a favorite among cyclists for its exceptional organization and support. Participants consistently praise the well-marked roads, the enthusiasm of community volunteers, and the abundantly stocked rest stops that provide ample food, sports drinks, and mechanical assistance to keep you fueled and moving forward. New for 2026, an elevated post-ride experience awaits with a fresh meal from local food truck Steve's Tacos, along with professional ride photos and a commemorative patch. Longer distance riders (100K, 150K, and 200K) will also enjoy a dedicated lunch stop at Aid Stations 3/4 featuring Steve's Tacos' specialty cold quesadillas.

Starting and finishing at Harris Park in Dodgeville, the Dairyland Dare promises a truly memorable and challenging day on the bike. Whether tackling the infamous climbs to accumulate over 13,500 feet of elevation on the longest routes or enjoying the picturesque scenery, this event stands out for its impeccable support and vibrant atmosphere. For those seeking an even greater feat, consider the "Driftless Double Dare," a combined challenge with the Horribly Hilly Hundreds.