The historic race has long been one of the most popular mountain bike events in America


The start of the race is impressive as it leaves Hayward, Wisconsin, with a huge field of riders.

The Chequamegon 40 is turning 40 years old this month with the running of the 2023 edition on September 16th. Not many races out there can claim to have been around (and thriving with sold-out fields) for that long! Relive some of the Chequamegon 40’s favorite Northwoods memories here, and check out the full history of the event here, and find more info about this year’s edition below.

The Chequamegon MTB Festival was born as a featured point-to-point 40-mile off-road event from Main Street Hayward, Wisconsin, to Lakewoods Resort in Cable, Wisconsin. Contrary to popular belief, Gary Crandall, aka “The Fatman” and soon-to-be long-time event director, did not dream up the event concept. However, he did race in it the first year and finished a very respectable 12th. Admittedly there were only 27 riders, but not bad for his first off-road race.

In scrolling through the history of the event in the links above, we read that America’s three-time Tour de France winner Greg Lemond entered the event over 30 years ago so he could compete in his very first mountain bike race. Here’s what the event’s historians reported about that appearance:

LeFat, LeMud, LeMond
This descriptive alliteration was the race weekend mantra of the early 1990s. Three-time Tour de France champion Greg LeMond attended and won his first mountain bike race in the rain-shortened Chequamegon 40. He returned in 1991 to defend his title in yet another weather-shortened 35-miler.

Not only did LeMond claim victory in the long race, in the days before the event in 1990 he caught a world-class line record bass in Lake Owen that was registered in Hayward’s National Fresh Water Fishing Hall of Fame.

LeMond’s attendance at the Chequamegon event was definitely one of the most memorable experiences for participants, volunteers, staff and spectators alike. His participation and championship brought a tremendous boost in media attention to the event.

40th Anniversary Panel

The organizers will be hosting a panel discussion with Dan Hunt, Gary Crandall, and other folks who have been a part of Chequamegon since the beginning. They will answer some questions about the origin of the race and how the race evolved over the years in their eyes. Friday, Sep 15th at 6 pm at the expo venue.

Reach out if you’d like to be put in touch with any of them for pre-event interviews.

All Types of Racers 

While the impressive pro racer fields boost the profile of Chequamegon, thousands of amateur riders take part each year. It’s these amateurs from all corners of life that make the race what it is and help sell out the fields year after year. In addition to the traditional 40-mile course, there is the 16-mile Short and Fat route as well as a 15-minute long fun race for kids.

This is a race that runs in both good weather and bad. Riders shouldn’t expect to come across the line looking the way they did when they started.

Midwest Life Time Grand Prix Athletes

Jenna Rhinehart is a Life Time Grand Prix athlete from the area and has been in the Chequamegon event twice in the past. She also owns and operates the Nicollet Bike & Ski shop in Mankato when not training and racing. In addition, Chequamegon champion Alexey Vermeulen had roots in the Midwest before he moved to Boulder, Colorado.

Course and pro prize purse 

The Chequamegon 40 follows the course of the famed American Birkebeiner Nordic ski race course. The “Birkie,” as most know it, attracts Olympic-caliber XC skiers to Wisconsin every winter. In the early fall, the trail turns into the perfect proving ground for cross-country mountain bikers, featuring fast trails that are punctuated with steep and punchy climbs. This makes the race a polar opposite to races like the Sea Otter Classic or Leadville Trail 100.

Whichever pro riders have the snap in their legs though will be eyeing the pro prize purse of $10,000. Both the women’s and the men’s categories pay out the following: 1st $2,500 | 2nd $1,000 | 3rd $750 | 4th $500 | 5th $250

Life Time Grand Prix Standings for 2023

Below are the current standings heading into Chequamegon. Keegan Swenson and Sofia Gomez Villafane hold solid leads, but look out for Bradyn Lange at Chequamegon. He won the men’s race in last year’s slick and muddy edition. Jenna Rinehart (mentioned above) is in a tie for 7th place in the series overall and is another rider to watch.

Here are the current standings in the 2023 Life Time Grand Prix.

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