Big Sky cyclist & school board member, Matt Jennings

Matt Jennings is an avid cyclist, school board member, and jack of all trades who left the flats of Waterloo for the mountains of Montana. He has lived in Big Sky since ‘94.

In the thirty years of bicycling around the Greater Yellowstone Ecosystem, Jennings recalled a few wildlife encounters from his years of pedaling down quiet roads, sometimes during dawn and dusk.

“I haven’t really had any close bear encounters. A couple springs ago, my friend Allen and I were cycling through the park before it opened for cars. We were going towards Mammoth from West Yellowstone. We got up to an open section of road and you could see buffalo coming down the road... Probably 8-10 coming down. We kind of pulled over, waiting there, and they just kept coming down the road at us, coming down the road at us, never really stopped. We were standing on the side of the road and there was nowhere really else to go... we did end up having to jump off the side of the road into the ditch kind of holding up our bikes as shields—like that would have done anything. They [the buffalo] kind of stayed on the road and thundered right by us. That was a recent, kind of scary... Holy s*#t, that was close,” said Jennings.

Matt grew up in the northeast corner of Iowa in a town called Waterloo. As the story goes, the town name comes from a guy named Charles Mullan. Mullan petitioned the town for a post office and had to choose a name. While flipping through a book of names for the U.S. Post Office, Mullan found Waterloo and it stuck.

“Boy, there is not a whole to tell,” said Jennings. “It was kind of just a regular childhood. Playing sports in high school and hanging out in the summertime. Growing up, you know, in the corn fields, tasseling corn as I was growing up throughout the years. Regular childhood I guess,” said Jennings. “We were never like a farming type family or anything. We were surrounded by it [farming],” said Jennings.

During the summertime, a teacher recruited Jennings and his friends to detassel corn. The students earned around $1000 bucks a month. “The furry, fluffy part, top of the corn—you actually walk through the corn fields and pick those off. Pretty exciting work,” laughed Jennings. “You just literally walked the miles of rows of corn back and forth.”

Back then, the main economic driver in the town of approximately 160,000 was a John Deere tractor factory. According to the John Deere museum, the company produced its first tractors in Waterloo around 1912. Over a century later, a large majority of Deere tractors still are built in Waterloo.

Growing up in the Midwest, Matt kept an eye out for tornadoes and got used to the blare of sirens on Fridays. “That just happened all the time [tornadoes]. I’ve been close several times but never had anything hit houses or anything where I was living. Definitely had to batten down several times. I’ve seen a handful in my lifetime from a distance and that’s as close as I want to get. It was just kind of second nature growing up there. Kind of expect it every summer at some point in time,” said Jennings.

Matt moved to Big Sky in 1994 following a year in Jackson Hole. He went to college at Iowa State in Ames. When he first arrived with his partner Erika, Big Sky felt much like a sleepy mountain town. There was nothing in the meadow, little to town center, and no condos at Firelight or Deer Run. “Moonlight was a place we used to go backcountry skiing, cat skiing. Nobody thought about Pioneer at the time. That was just another mountain up in the area that’d you’d just go explore off Buck Ridge,” said Jennings.

Twenty-eight years later, Jennings is a property manager for the Yellowstone Club and serves on the Big Sky School District board. “I have a portfolio of 10 homes that I manage up in the Yellowstone Club. I work with families, keep the houses running, take care of the maintenance, line things up for people, coordinate quite a bit of stuff like work to be done, and keep an eye on places,” said Jennings, who has worked for the YC for the last six years. Jennings also worked for Moonlight Basin, the Resort for about a decade, and managed a variety of ski and repair shops.

When Matt is not tied up, he is typically on a bicycle, thinking about bicycles, or planning the next ride. Earlier this summer, Matt and four friends from Big Sky—Alan McClain, Mitch Hammel, Mike Ketschek, and John Flach—bikepacked across Washington state. They started in a little town on the Pacific Ocean called La Push, cycled through the Olympic Peninsula, weaved through Seattle and Snoqualmie, and then pedaled East to the border of Idaho. In total, the small crew bicycled across the state in eight days.

“It was all bikepacking. We had all of our own gear, camping gear, self-supported, and it was mainly on gravel roads and single track, kind of off the beaten path,” said Jennings. Matt is already planning another ride along the Tour de France with his brother in 2022. The two plan to fly into Geneva, ride sections of the course, and then watch the race.

With the holidays coming up, Matt shared a story about the best Christmas present he received in junior high. “I got my first real pair of skis… They were Atomic Arcs, they were the soft SLs, and they were bright yellow, kind of neon colors. I think I got my first pair of stretch pants at that point too. And rear entry boots, Salomon SX 80s, I remember red. I thought I was all that living in Iowa. I think I even got a fluorescent pair of Oakleys at that Christmas too,” laughed Jennings. 

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