In early autumn, the town of Spearfish, South Dakota, is overtaken by the Dakota Five-O 2026. This adrenaline-pumping mountain bike race promises 50 challenging miles of intense riding, enticing not only with its distance but also with its technical complexity. This is not a race for the faint of heart or the casual biker – it requires true grit, as the race encompasses about 90% singletrack, a daunting 6500+ ft of climbing, and treacherous technical sections. The Dakota Five-O 2026 is considered by our team to be one of the Best Mountain Bike Events in the Midwest.

The Dakota Five-O is unique partly because of its “Lollie-pop loop” format, which commences with a mass rollout from Spearfish City Park. As bikers ascend Tinton Road, they merge onto the snaking, sleek Tinton Trail single-track. The course’s direction reverses every year. In even years, riders experience the course clockwise; in odd years, it’s the opposite. This rotation ensures the route always feels fresh, throwing new challenges at returning riders.

For even years, the track dives into the gully known as Twin Bridges after the initial climb, leading riders to the first aid station at Big Hill Trailhead (mile 11). The route winds through Cardiac Bypass, Recovery Ridge, and the Old Baldy trail system. Riders must also tackle Taco Alley, Sheep Steeps, and Dakota Ridge. A high point (literally!) for many is the Bacon Station at mile 38, where riders can indulge in a well-earned bacon snack and a PBR.

The odd-year course introduces bikers to the rapid K-Nectar trail, followed by the steep Dakota Ridge. After the challenge of Stadium Ridge, riders cruise through Old Baldy, Recovery Ridge, and then the Big Hill Trail system. The familiar Bacon Station greets racers at mile 37. There is a race cutoff at Old Baldy (1:30 pm during even years) and a 2:00 pm cut-off for odd years.

Regardless of the year, every finisher is welcomed back to Spearfish City Park with music, food, and a refreshing cold brew. Cyclists can earn cash prizes for the top five men’s and women’s finishers, custom trophies and special prizes.

The weekend boasts a line-up of events, including a pre-party on Friday with live music, a Strider Bike race, and an industry expo. Saturday focuses on race packet pickups, and Sunday’s post-race celebrations begin at 11 am in Spearfish City Park. An awards ceremony at 4:30 pm recognizes outstanding performers. An evening after-party at Killian’s Tavern offers racers and attendees a relaxed space to wind down.