We’re excited to announce a new partnership between the Horribly Hilly Hundreds and the Dairyland Dare!

Two iconic Wisconsin rides, one shared love of steep climbs and big days on the bike. Riders who take on both events this season can join the Driftless Double Dare, a brag-worthy challenge celebrating grit, community, and leg-burning hills from Blue Mounds through the Driftless Area.

Register for any distance at Dairyland Dare (50K, 100K, 150K, or 200K) taking place on August 1, 2026, and the individual event at Horribly Hilly Hundreds, happening on June 13, 2026, for a bundled price of $220!

Complete both rides and you’ll earn special recognition, plus a custom, one-of-a-kind slate coaster and commemorative patch available for pick-up at Dairyland Dare. Proof that you didn’t just ride the hills…you survived them.

Consider this your friendly nudge to double down on the hurt, in the best possible way.