The Chequamegon 40

Nestled in the scenic terrain of Wisconsin’s Northwoods, the Chequamegon 40 bike race has grown from a local experiment into one of America’s premier off-road cycling events. Known for its challenging route, passionate community, and deep roots in mountain biking history, the event is the highlight of the Chequamegon Mountain Bike Festival. It attracts both elite and amateur riders from across the country and beyond. Race day this year will be held on September 13.

Humble Beginnings to the Modern Day

The race began in 1983 as a collaborative effort between staff at two local resorts - Telemark and Lakewoods - who sought to extend the tourism season beyond summer. Their quirky idea was to run a 40-mile mountain bike race mostly along the American Birkebeiner cross-country ski trail from downtown Hayward to Cable. Despite minimal promotion, 27 adventurous cyclists showed up for the inaugural event. Since then, the event’s unique point to point format, beautiful Northwoods setting, challenging course, and community atmosphere have led to rapid growth. The growing popularity of mountain biking at the time, along with NORBA (the National Off Road Bicycle Association, a former governing body of mountain bike racing in the US), sanctioning the Chequamegon 40 as the first Midwest Off Road Championship only a couple of years after its first running, led to further growth and participation by off-road cyclists, both amateur and professional. Several prominent cyclists raced at Chequamegon in its first decade of existence, including cycling legend and Tour de France winner Greg Lemond, who raced and won the event in the early 1990s.

While known for many years as the Chequamegon Fat Tire Festival, the event was renamed the Chequamegon Mountain Bike Festival several years ago to avoid confusion with fat-tire bike events (which weren’t really “a thing” in cycling culture 3-4 decades ago), even though you’ll definitely see fat bikes in action that weekend!

Fast forward to 2025, the Chequamegon 40 is also one of six events in Lifetime’s Grand Prix series of off-road races. The Grand Prix is made up of a select group of male and female professional riders, competing in a mix of prominent gravel and mountain bike races. Both of last year’s Chequamegon 40 elite/pro category winners, Sofia Gomez Villafañe in the women’s and Keegan Swenson in the men’s, are competing in the Grand Prix series this year, so you can expect to see them toe the line again in defense of their titles this September. The Chequamegon’s relatively short length (at least when compared to the other events in the series) and nature of the course means that raw power will likely be more important for the racers competing than technical riding expertise on this day.

The People’s Race

While professional cyclists may garner more of the media attention on race day, the heart & soul of the event, along with the vast majority of the nearly 3,000 cyclists that compete here annually, remains the amateurs, weekend warriors, and the celebration of the off-road cycling community held here each fall. As stated on the event website, “Some compete in the headliner event for the chance to be called champion. But most are in it for the adventure and personal challenge”. In addition to the 40-mile point-to-point race, participants wanting a shorter distance can choose the “Short and Fat” 16-mile race, a loop route that starts and ends in Cable. The little tykes aren’t left out of the Cheq fun either, with a chance to get dirty at the “Little Loggers” bike ride. This free event for kids up to 13 years old (with three separate kids’ age categories) takes place that Friday on a one-mile loop course. These additions over the years have made the Chequamegon Mountain Bike Festival more inclusive and family-friendly. A newer addition to the festivities is the stein holding contest. According to Lifetime’s Jack Shields, “This is a new activity that we started last year with great success. The idea is that a group of 10 people hold a Stein out at arm’s length, the last person who can keep their arm up wins!”

A Unique Race on Challenging Terrain

As previously mentioned, much of the route is held on the American Birkebiener ski trail, a grassy path of rolling hills through the woods. Although a wider berth than typical singletrack, the punchy hills present a challenge, and riders have shared that there is still a fastest line to be found within the grassy pathways (and of course, the rainy/muddy years present a whole different set of issues). The route also includes rugged gravel and forest roads, along with other assorted dirt and snowmobile/ATV paths through beautiful woodlands filled with maple, pine, aspen, and birch. Some of these “pinch points” where the course narrows, especially on iconic parts of the route such as the steep and rugged Seeley Fire Tower climb, are locations where a pack of racers may separate from one another on the push towards Cable.

To find out more or register for the Chequamegon Mountain Bike Festival’s 40-mile race, 16-mile Short & Fat, Little Loggers, or a schedule of activities, visit www.cheqmtb.com.