Ski With an Olympian at These Ski Resorts

There’s nothing like a full ski day of shredding down new terrain, finding powder stashes, and racking up vertical. That is, unless you added the thrill of getting to do all that while skiing with an Olympian. Ski resorts around North America offer just the chance to ski or ride with Olympians. Whether you want to fine-tune your technique, get some insider tips to the mountain, or simply enjoy a one-of-a-kind day on the mountain, skiing with an Olympian transforms a good ski day to one of the most memorable ski days of your life. Below, we share where you can live out a once-in-a-lifetime experience.

Where To Ski With An Olympian

Deer Valley Resort, Utah 

Ski with one of several Olympic snowsport athletes at Deer Valley in Park City. Deer Valley Resort offers various packages for individuals, families, and groups to ski with an Olympian for either a full or half day. Note that this package is not a lesson and participants must already have some level of skiing ability. Skiers must be at least 7 years old and children under 12 must be with an adult. 

Pricing for the 2024/25 season is $2,570 for a full-day session and $2,845 during peak season. A half-day session is $1,470 and $1,655 during peak season. Guests can fill out a request form on Deer Valley’s website to book. Deer Valley’s Olympians include: 

• Shannon Bahrke: A silver and bronze medal-winning mogul skier, she was a three-time Olympian and the 2003 Overall World Cup Champion. 
• Kris Feddersen: A freestyle skiing pioneer and three-time Olympian who coached the 1998 U.S. aerial ski team to two gold medals. 
• Kaylin Richardson: A four-time national alpine champion and two-time Olympian who later dominated the freeskiing world and appeared in Warren Miller films. 
• Trace Worthington: A U.S. Ski Hall of Famer and two-time Olympian who won 37 World Cup races and has been a Deer Valley local for more than two decades. 
• Jillian Vogtli: A two-time Olympian and mogul skiing innovator who was the first woman to perform a cork 720 at the Olympic Games. 
• Chris Waddell: A legendary monoskier, Paralympic athlete, and wheelchair racer who summited Mount Kilimanjaro nearly unassisted in 2009. 
• Ashley Caldwell: A four-time Olympian and Olympic gold medalist in freestyle aerials, Ashley made history with a world-record quadruple-twisting triple flip at the World Championships. 

Crested Butte Mountain Resort, Colorado 

Crested Butte’s Ski with an Olympian program features Wendy Fisher, one of the most accomplished figures in the world of freeskiing. Wendy Fisher, a world champion in big mountain freeskiing, has a storied career that includes competing in the 1992 Olympics in Albertville, France, winning the 1991 U.S. Nationals overall title, and taking home two World Extreme Freeskiing titles. She has also been voted the Best Female Skier of the Year by Powder Magazine on multiple occasions.

Now a full-time resident of Crested Butte, Fisher offers private ski lessons for guests to explore the mountain’s most challenging terrain with a true legend of the sport. Limited to six people per session, these lessons provide an exclusive chance to improve your skills with personalized coaching from an expert. Full-day and half-day sessions are available, with prices ranging from $935 to $1,335, depending on the season. Call (970) 349-4765 to book or visit Crested Butte’s website for more information.

Jackson Hole, Wyoming

Jackson Hole is a renowned ski destination, as evidenced by OnTheSnow users rating it the Best All-Mountain Terrain Resort. It simply doesn’t get better than skiing with an Olympian at one of the best resorts in North America. Jackson Hole Mountain Resort offers an exclusive opportunity to ski with two world-class athletes, Tommy Moe and Resi Stiegler. Both have called Jackson Hole home for over twenty years. Their deep knowledge of the mountain and Olympic backgrounds make for an unforgettable experience.

Tommy Moe, an Olympic downhill skiing gold medalist, provides a thrilling experience for intermediate to expert skiers. He’ll guide you through both in-bounds runs and Jackson Hole’s renowned backcountry terrain, sharing insights from his Olympic career and tips to enhance your technique.

Resi Stiegler, a three-time Olympian and slalom specialist, offers a unique perspective with her insider knowledge of the resort. She is the daughter of Jackson Hole’s first Ski School director and has a deep-rooted connection to the area. Known for racing with tiger ears on her helmet, she brings a playful and approachable teaching style to her sessions. Her slalom expertise and local knowledge will help you navigate Jackson Hole’s technical lines while having fun and improving your skills. These private sessions are available for intermediate to expert skiers.

A full-day private lesson costs $1,550 during the regular season and $1,635 during peak season, with half-day sessions starting at $1,195. For even more personalized experiences, guests can book the “Ultimate Ski Day” (with Tommy or Resi from breakfast to dinner) or Resi’s “Raceday,” in which skiers ski on a private racecourse. To book your Ski with an Olympian experience, visit the Jackson Hole website or call the Mountain Sports School at 888-697-6949.

Whistler Blackcomb, British Columbia

Whistler Blackcomb guests can ski with a whole lineup of Olympians. Co-created by former Ski Cross athletes Davey Barr and Julia Murray, who have deep ties to the Whistler community, the program connects participants with Olympic-level expertise. Their vision, supported by their family’s long history in Whistler’s skiing scene, has evolved into one of Whistler Blackcomb’s most popular experiences.

The program offers different packages for skiers and snowboarders. Full-day private sessions start at $1,405 (CAD) during the off-peak season and rise to $2,500 during peak and holiday times. Whistler Blackcomb’s Olympic roster includes:

• Ashleigh McIvor: Ski Cross, Vancouver 2010 Olympic Gold Medalist. A Whistler local and Olympic gold medalist, Ashleigh shares her love for skiing and local terrain while offering an unforgettable mountain experience.
• Dave Duncan: Ski Cross, Vancouver 2010, Sochi 2014, Pyeongchang 2018. From London, Ontario, Dave has more than 20 years of experience skiing in Whistler. He guides guests through Whistler Blackcomb’s hidden gems and shares his Olympic journey.
• Anna Segal: Slopestyle Skiing, Sochi 2014. Originally from Melbourne, Australia, Anna now lives in Pemberton, BC. She leads skiers through diverse terrain while sharing her Olympic experience.
• Julia Murray: Ski Cross, Vancouver 2010. A Whistler local with Olympic experience, Julia offers expert guidance and helps skiers build confidence on the slopes.
• Kristi Richards: Freestyle Mogul Skiing, Torino 2006, Vancouver 2010. A two-time Olympian from Summerland, British Columbia, Kristi offers expert mogul coaching and fun mountain adventures.
• Anastasia Skryabina: Alpine Skiing, Vancouver 2010. A Whistler native, Anastasia provides expert alpine guidance, sharing her Olympic experiences while exploring all types of terrain.
• Robbie Dixon: Alpine Skiing, Vancouver 2010. A Whistler local, Robbie combines Olympic racing experience with his knowledge of the mountain, offering an unforgettable tour through Whistler’s diverse terrain.
• Kelly Ringstad: Freestyle Mogul Skiing, Salt Lake City, 2002. Kelly, who hails from Vancouver, has 17 years of coaching experience, helping skiers improve their technique on Whistler’s moguls and parks.
• Tami Bradley: Freestyle Skiing, Moguls, Nagano 1998, Salt Lake City 2002. A North Vancouver native, Tami shares her Olympic mogul experience while coaching skiers of all levels on Whistler’s slopes.
• Mike Janyk: Alpine Skiing, Slalom, Torino 2006, Vancouver 2010, Sochi 2014. A Whistler local, Mike brings Olympic slalom expertise to his mountain tours, helping skiers improve their technique and explore Whistler.
• Rob Boyd: Alpine Skiing, Downhill, Calgary 1988, Lillehammer 1994, Salt Lake City 2002, Turin 2006, Vancouver 2010. A former Olympic downhill racer, Rob guides skiers with stories from his legendary career and expert insights into Whistler’s terrain.
• Marie-Pier Prefontaine: Alpine Skiing, Super-G and Giant Slalom, Vancouver 2010, Sochi 2014. Marie-Pier offers Olympic-level guidance from Quebec while showcasing her favorite spots on Whistler’s diverse terrain.
• Ryan Johnson: Freestyle Skiing, Moguls, Nagano 1998, Salt Lake City 2002. A Squamish native, Ryan brings his freestyle skiing expertise to Whistler, offering coaching and fun adventures for skiers of all levels.

To book this once-in-a-lifetime experience, guests can email Whistler Blackcomb’s Concierge department at wbmyconcierge@vailresorts.com or call the resort’s booking lines. Early booking is highly recommended, as pricing and availability are subject to seasonal changes, especially during peak holiday periods. More information can be found on the resort’s website.

Mirror Lake Inn Resort & Spa, Lake Placid, New York

Guests of the Mirror Lake Inn Resort & Spa in Lake Placid have the opportunity to ski with Andrew Weibrecht, a two-time Olympic Alpine skier who won bronze in 2010 and silver in 2014. He is known for his grit and success on the world stage, particularly in the super-G event. This one-of-a-kind package includes a private ski session with Andrew Weibrecht on the nearby Whiteface Mountain, followed by a relaxing stay at the Inn. Weibrecht grew up skiing Whiteface and has enjoyed sharing his family’s inn and home mountain with guests. 

“I have a great love for skiing and a real appreciation for this area,” said Weibrecht. “Adirondack Park is such a unique, special, and little-developed area. I spent my whole youth skiing here, and it’s really fun to share that with different guests, especially those just getting interested in skiing. It’s a great experience for those on the East Coast, too, since there aren’t many programs like this here, and it really helps set us apart.”

On average, Weibrecht skis with about 20 groups per season and welcomes everyone from beginners to experts to participate. The cost is $350 per hour with a two-hour minimum for up to two people. If more people want to join, it’s an extra $75 per person. The hotel is also set up with a rental shop for people who need gear. The experience is offered exclusively to Mirror Lake Inn guests and can be added to any hotel reservation. You can inquire about availability for the Ski with an Olympian package via the Mirror Lake Inn website or by calling the hotel’s concierge. Note that lift tickets are not included.

Hero image ©Deer Valley Resort