In Jackson Hole and Beyond, Madison Rose is a Force of Nature

Featured Image: Stephen Shelesky | Skier: Madison Rose Ostergren | Illustration: Christian Johansen

At 5’6″ Madison Rose Ostergren might not be the tallest in the lift line, but she’s likely the fiercest. You’ve probably seen the fiery redhead on the internet. If you’re lucky, you may have seen her ripping around Jackson Hole Mountain Resort with the crew. Luckier still, you might have caught her in the backcountry, tackling some of the gnarliest lines in the Tetons. Catch her if you can, for she’s an unstoppable force, with an infectious spirit that has captured the heart of the ski industry.

Ostergren didn’t grow up in the mountains she now calls home. Hailing from Traverse City, Michigan, Mads—as she’s lovingly known in some circles— swears she was sprinting “straight out of the womb.” And we believe her. With dreams as big as her six-pack at age six—likely from lifting up her dad’s friends—everything was a competition. Judging by the home videos, she won most of them. As she grew, her competitive drive was fueled by strong supporters, particularly her mother, Tracy.

“She told me I could do anything I set my mind to, and I believed it,” says Ostergren. “She let me run free, try my hardest and just do my thing.”

After moving west in high school, Ostergren raced downhill at Utah’s Westminster University and began to catch photographers’ eyes while scrambling around the Wasatch. But it was when she moved farther north, to Jackson Hole, that her skiing dreams really took off.

“It’s the best resort skiing in America—no questions asked. If you want to be a pro skier or just a really freaking good skier, you come to Jackson. The terrain is unbeatable—steep, sustained, rocky and not for the faint of heart.”

All smiles on a pow day | Photo: Stephen Shelesky

She’s not wrong. With over 4,000 feet of vert, the options inside the resort are endless— from sustained, steep groomers to inbounds couloirs, awe-inspiring cliffs and everything in between. That’s all before going out of bounds, where some 40 square miles of rowdy Teton topography stretch to the north and south. The north boundary of the resort abuts Grand Teton National Park, where the iconic, namesake peak smiles down from a towering, 13,775’ summit.

It’s no wonder Jackson Hole Mountain Resort and the Tetons have produced some of the best skiers and ski mountaineers in the world. With lines pioneered by icons like Doug Coombs and Bill Briggs (who skied the unskiable Grand in 1971), it’s safe to say this geography has been pivotal in the growth of US extreme skiing. Madison is proud to be a part of this history as she adds her own chapter to ski culture.

“Having this as my backyard is a dream. The terrain here tests you as a high-alpine athlete and ski mountaineer. It’s where you can truly push your limits.”

Jackson’s athletes are constantly raising the bar and Ostergren is no exception. But the community’s passion for skiing runs deeper than just technical prowess. “The mountains make you a better skier, but the people push you to be more soulful and conscious in how you move through them.”

Visit the resort on any given day and you’ll see jaw-dropping feats—bumps smashed harder, cliffs sent bigger and trenches laid deeper than perhaps anywhere in the US. But you’ll also see more smiles, high fives and camaraderie. Ostergren is at the heart of this community, embodying that depth. There’s more to her character than big lines and fast skiing.

She’s a skier’s skier that’s passionate about every aspect of the sport. “I want to be as versatile as I can be: bumps, groomers, ski mountaineering, skijoring, big mountain, shralpinism, whatever!” she proclaims. “I love it all and I want to ski the biggest mountains in the world. I’m fiercely driven and believe the road to success is paved with goal setting, hard work and gritty determination.”

A casual weekend outing for Ostergren | Photo: Cam McLeod / Location: Grand Teton National Park

Yet, the “Teton Hard B*$#h,” as she proudly identifies, must balance herself with a calmer side. Based on her social media presence, it’s easy to view Madison as an ever-burning ball of energy, but an old soul resides inside—the kind who’s tucked into bed by 8pm—if only to wake at 4am for an alpine start. While she’s often the life of the party, she also treasures quiet time at home, whether that’s playing an instrument or cooking dinner for a friend.

Resting as hard as she trains is one of her greatest challenges, Ostergren admits, but she’s committed to it. This quest for balance has shaped her into one of the hardest-charging women in the industry, a fact not lost on her fellow athletes.

“Madison is an absolute force of nature,” says professional skier Ingrid Backstrom. “She brings her whole heart to whatever she does and puts in the work behind the scenes. The lines she’s flashing in Jackson are serious, technical and masterful, yet she somehow makes these superhuman feats look easy-breezy.”

Backstrom goes on to highlight another aspect of Ostergren’s personality; one that really sets her apart. “She brings an artist’s creative eye to her lines, and a dancer’s rhythm that enables her to shred them with grace. She’s the type of person who is so good at everything that it could be intimidating. But she leads with her heart and brings everyone along in her magical, radiant frequency. I’m completely inspired by Madison, on the mountain and off.”

Ostergren finds the rhythm in skiing and music | Photo: Taylor Fasolo

Madison’s radiant frequency electrifies everything she does. If you find yourself at Jackson’s Wort Hotel on a Tuesday night, you’ll hear rowdy bluegrass tunes and see a flash of red lighting up the dance floor, lifting up everyone around her. Ostergren is right up there with the best dancers in the valley, teaching many-a-novice how to country swing, including this author.

Yet her talents extend far beyond skiing and dance. This off-season, she’s pouring her creative energy into recording her debut album. Her music, a blend of indie Americana and pop-rock, channels artists like Maggie Rogers and Kacey Musgraves, while evoking the timelessness of Bonnie Raitt or Gillian Welch. She sings and plays multiple instruments on the record, which she’s also producing.

From playing music, dancing and drawing, to painting, baking and cooking, Madison’s creativity flows in many directions. She even got a drone to try her hand at aerial photography and in one highly entertaining chapter, bought and began retrofitting a small school bus. The construction phase didn’t go as planned but yielded some valuable lessons, and proved yet again that if she wants to, she will.

Madison is a uniquely creative mind—a blend of badass mountain chick and rockstar Broadway babe. One might even call her a Renaissance woman. Her diverse skillset echos that of aforementioned Bill Briggs, who not only made the first ski descent of the Grand Teton but also founded the Jackson Hole Hootenanny, a weekly musical cabaret that has showcased Jackson’s brightest musical talent for over 30 years. Madison has performed there numerous times.

Madison and her ski partner, Jim Ryan, tear up the groomers at Jackson Hole Mountain Resort | Photo: Stephen Shelesky

“The depth of her talent is insane,” says fellow pro skier Amie Engerbretson. “Yes, she totally rips on skis, but her exuberance, dancing, voice, energy and infectious personality make her truly one-of-a-kind. I have never met anyone with Mad’s energy.”

However radiant, it’s a tall order to be expected to be exuberant all the time, and this energy comes at a cost. While she was born to perform, Ostergren’s novel personality hasn’t always been met warmly and she’s faced her share of critics.

“My accomplishments have been questioned,” she notes. “Along with my strength and my ability to make it as a professional skier—all of it.” Even her authenticity has been challenged, which can dim anyone’s light. Still, Madison continues to operate on a fundamental principle: lead with love.

With a chip on her shoulder, she acknowledges a mix of naivete and a little impulsivity. “The critiques become fuel, which intensifies my motivation.” And with a wry smile, she adds, “Watch me.”

In a recent Fifty+ article, ski industry leader Cody Townsend states what he believes is the job of a professional skier. Using Shane McConkey and an aggressive, California surf culture as his backdrop, Townsend explains, “Pro skiers are egotistical to varying degrees. Some are worse than others. To become a professional athlete, one must have an inherent belief in their own capabilities—a belief so strong that it borders on pure-blown egotism.” He cites early MSP films, in which McConkey’s joy between takes, goofy smile and self-deprecating humor created an aura that made skiing seem like the single most fun activity on Earth. He concludes that the singular job of the professional skier is to inspire. If we take Cody’s word for it, Madison is doing a damn good job.

Jackson’s Big Red Tram provides access to 2,500 acres. Whether that’s a playground or a training ground is up to you | Photo: Stephen Shelesky

Big personalities tend to ruffle feathers and those in the spotlight leave themselves open to criticism. Yet maintaining a course true to oneself while remembering to lead with love? That’s certainly worth celebrating.

“Madison’s excitement and drive to be the best version of herself is contagious,” says pro skier Michelle Parker. “She’s strong, capable and endearing. Her technical ability on skis is hard to match, but in addition to her athleticism, she’s bright, smiles big and easily admits that she’s human. She possesses a touch of femininity that we rarely see from people doing big things in the mountains. It’s refreshing and beautiful, intoxicating and vulnerable. I absolutely adore her.”

We could all use just a bit of what Madison has in droves. It ain’t always perfect but it’s authentic. In a world of followers, it takes a brave soul to be original. Whether skiing down Thunder Bumps at JHMR, singing around a campfire or dancing the night away, she’s proof that you don’t have to fit a mold to be successful. You just have to bring you whole self. And that’s exactly what she does.

“Madison Rose is like the weather,” says JHMR athlete and Ostergren’s ski partner, Jim Ryan. “You can complain about her all you want, but she’s dictating your day, and it’s best you plan around her. Even better, admire her. She’s lightning and sunshine. She’s a colossal pain in my ass, but I wouldn’t give her up for the world. Who would give up weather? She’s a g*d@#m force of nature.”

JACKSON HOLE MOUNTAIN RESORT SPECS

BASE ELEVATION: 6,311 ft

SUMMIT ELEVATION: 10,450 ft

VERTICAL RELIEF: 4,139 ft

SKIABLE ACRES: 2,500

CHAIRLIFTS: 13

AVG. ANNUAL SNOWFALL: 458 in

TRAVEL LOGISTICS

GETTING THERE

Jackson Hole airport (JAC) has nonstop flights from 12 major US cities. From there, it’s an easy, 15-minute drive to the town of Jackson and just 30 minutes to Jackson Hole Mountain Resort. By car or shuttle, Jackson is 4.5 hours north of Salt Lake City, UT and 4 hours south of Bozeman, MT.

RESORT TIPS

Jackson Hole Resort Lodging

Whether you’re looking for a one-bedroom condo in Teton Village or a massive house for you and your friends, the friendly staff at JHRL can help you find the perfect spot.

Jackson Hole Resort Reservations

JHMR’s official reservations service has experts at the ready. They can help you book mountainside accommodations at the Gravity Haus or line you up in-town hotels like Mountain Modern, just 2 blocks off Jackson’s town square. Additionally, they can help you plan your entire dream trip, including flights, local transportation, ski rentals and other activities around the valley.

RESORT TIPS

Reserve Dates Early

There were a few years in which tram lines got a little out of hand at JHMR. To its credit, the resort began limiting daily capacity to deliver a better experience and that mean it’s best to reserve lift tickets early. IKON and Mountain Collective passholders also need to make advanced reservations.

50% off Lift Tickets

During select weeks, passholders from any resort in the world can get half price lift tickets. JHMR’s Golden Ticket deal applies between November 29-December 25 March 17-April 13, 2025.

JH Insider App

JHMR’s app that helps you navigate your day at the resort. Useful features include daily snow and weather reports, real-time parking info, current lift and mountain status and live webcams.

This story originally appeared in FREESKIER Magazine Volume 27 Issue 2. Click here to subscribe to FREESKIER and have print copies (yes, real print magazines!) delivered right to your door.