In a land where diesel-powered adventure reigns, the town of Hayward, WI welcomes the onslaught of “granola fueled forest fairies” twice a year. Each February, the surrounding area fills with world-class Nordic skiers vying for Birkibeiner gold, while in mid-September, the fat tire set rolls in for the Chequamegon 40 mountain bike race—both run on the same course. According to locals, the mountain bikers are a bit more tolerable because at least they drink beer.

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Chequamegon 40 Mountain Bike Race

Chequamegon 40

In a land where diesel-powered adventure reigns, the town of Hayward, WI welcomes the onslaught of “granola fueled forest fairies” twice a year. Each February, the surrounding area fills with world-class Nordic skiers vying for Birkibeiner gold, while in mid-September, the fat tire set rolls in for the Chequamegon 40 mountain bike race—both run on the same course. According to locals, the mountain bikers are a bit more tolerable because at least they drink beer.

Earlier this month, I road tripped from California to Wisconsin, stopping off at mountain bike meccas such as Crested Butte, CO along the way. I grew up spending weekends and summers in Hayward, at our family’s cabin on Round Lake. Lumberjack festivals, tubing, water skiing, fishing, snowmobiling, snowshoeing, and s’mores filled our days, but I never once raced the Chequamegon, mainly because I didn’t get into mountain biking until a few years ago. This year, I knew I had to make the pilgrimage back and set things right.

The first Chequamegon race was held in 1983, with 27 riders lining up at the start. Today, over 30 years later, 2,100+ participants are selected each year in a random lottery to take part in this 40-mile challenge, run each year on Saturday of the Chequamegon Fat Tire Festival weekend. While a few pro riders compete for the chance to be called champion, it is the amateur athletes, in it for the personal challenge, fun, and adventure, that make up the bulk of the race field.

Chequamegon 1983
Chequamegon 1983-gym shorts over sweat pants, duck boots, handle bar bags, and blue jeans. Photo courtesy of CFTF.

The Chequamegon National Forest features rolling glacial terrain that not only offers a beautiful backdrop, but also makes for fun and challenging riding. Much of the money raised from the Fat Tire Festival goes towards CAMBA to help build and maintain over 90+ miles of pristine singletrack and a network of 300 miles of bike trails in northern Sawyer and southern Bayfield Counties.

I was surprised on just how much climbing is to be had here—the constant rolling terrain means you can net similar elevation gains over the course of a 20 mile ride as you can with a couple long uphills back home in Northern California or even Colorado. The singletrack reminds me of riding in the Northeast, with plenty of rocks and roots, bridges, and technical trail sections thrown in to keep things interesting along the flowy, packed dirt.

We pulled up to the cabin the weekend before the race only to find a fierce storm with winds over 70 mph and hail had ripped through the area earlier that morning. Enormous trees were down everywhere—on houses, sheds, and trails. Projectile hail had damaged roofs, windows, and boats, while wind ripped docks up out of the water and threw them clear onto the lake shore. It was a mess.

Land managers, area volunteers, and paid trail staff worked tirelessly to open the Chequamegon trails and get them race-ready for the following weekend—assessing damage, scheduling clean up crews, and planning for necessary course re-routes. The trails were wet, muddy, and full of debris. Even though it created quite a few bottlenecks, at least for those of us starting at the back of the pack (as a first time rider, I was given the last starting gate), I found the singletrack re-routes a fun break from the grassy and often muddy Birkie trail and rocky ATV/Snowmobile roads.

Chequamegon 40 Strava

The temperature read 36 degrees the morning of the race, with a high predicted that day for around 50. Fall had arrived with a vengeance to the Northwoods, but provided the perfect weather for riding hard.

After a mass roll out through the streets of Hayward, the pack started to spread out once we hit the Birki Trail at Rosie’s Field. Apart from some major bottlenecks at deep mud puddles and the aforementioned singletrack, you eventually got into a nice pace, ebbing and flowing with the same small group of people for much of the race. I rode for quite a few miles with a Canadian on a fat bike who had driven down from Ontario just for the weekend.

At around mile 26 you hit the infamous Seeley Fire Tower road—a stair step climb of 4-5 steep, rocky hills, one right after another. Most people resign themselves to hike-a-bike up this section, while a few brave and strong souls power through, burning lungs and legs in the process.

The one cruelty of the race is that you think it is all downhill into Telemark from the top. But after a fast descent, quickly losing all elevation, you have to gain all the elevation back again. Around mile 27, I started to notice my back-end was bouncing even though I kept the rear shock locked out. I was progressively getting slower even though I felt strong and was pushing hard. Did I need more food? Was my suspension playing tricks on me?

Chequamegon Fat Tire

Bouncing along, I eventually noticed my back tire continually sliding out from under me, especially on climbs. My worst fear had come true—I had a flat. My rear tire had been slowly leaking the entire ride until it finally gave out.

I pulled over to asses the situation. No noticeable puncture damage to the actual tire so it was probably a tiny pinch flat. I had only 10 miles to go to finish the race so I hoped that I could just pump some air in to get me across the finish line, stopping to top up along the way if need be. When I opened up my tool roll to get started, my heart sank as I realized I had the wrong inflator for the CO2 cartridges. Rookie move for not checking the night before to make sure everything in the tool roll itself was in order.

Luckily, a very nice man stopped to let me borrow his inflator and I was eventually off again. It wasn’t long before the slight bounce came back, but I knew I would make it to the end. Climbing the last hill into Telemark and bombing down the ski hill through crowds of cheering spectators was a memorable way to finish the race. I had finally ridden the Chequamegon 40.

A huge thanks goes out to the hundred of volunteers that make this event run smoothly—from all those that whip you through registration, to the hearty souls out on the trail making sure you don’t take a wrong turn and handing you donut holes, bananas, water, and energy drinks as you ride on by.

Let’s hope I am just as lucky in the Chequamegon 40 lottery next year.

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