When Taylor Ogilvie took his first job out of college at Colorado’s huge Vail Ski Resort, which covers more than 5,000 acres and has a vertical drop of nearly 3,500 feet, he had no idea he’d be embarking on a career that would lead him back to his local ski “hill.”
That was never the plan, said Ogilvie, who became general manager of Wilmot Mountain in Kenosha County, Wisconsin (wilmotmountain.com) last January after the resort was bought by Vail.
Since the purchase, Vail has invested more than $13 million to upgrade Wilmot. The results include three new four-person chair lifts, the renovation and expansion of existing buildings and a new snow-making system – among other major improvements.
“To be able to reinvent the mountain and guest experience at my home hill is incredible,” Ogilvie said. “I can’t wait for everyone else to experience it.”
Wilmot, which has a vertical descent of 230 feet, is in Wisconsin, sits directly on the Illinois line and borders the Lake County Forest Preserve. It’s in an almost ideal spot for a day skier area, located about 45 minutes from Milwaukee and roughly the same amount of drive time from many northern Chicago suburbs. Lake Geneva is less than 20 miles away.
Vail owns two other Midwest resorts and operates nearly a dozen others in the American West and British Columbia. Vail Epic Pass holders can ski at their local areas, as well as all of the company’s other resorts.
Ogilvie grew up in Lincolnshire, a northern Chicago suburb that’s about 30 miles south of Wilmot. He first snowplowed down a slope at Vail when he was 4 on a winter trip to the Rockies with his parents.
But Wilmot was his default ski area as a youngster and he figures he went there at least 50 times growing up, along with other Wisconsin resorts such as Tyrol Basin, Cascade or Devil’s Head resorts.
“It was a family tradition that we would go out West to ski at either Vail or Beaver Creek and sometimes Breckenridge,” said Ogilvie, who attended the University of Colorado at Boulder and skied every weekend he could during winters.
He graduated from CU in 2000 with a degree in history and immediately moved to Vail, where he got a job cooking at an outdoor grill. When winter arrived, he took a position as a children’s snowboard instructor.
Within a year, he was a supervisor and soon was promoted to run the whole youth program at the neighboring resort of Beaver Creek. By 2008 he was ski school manager at Lionshead, part of Vail. And in the summers he was managing capital construction projects on the mountain.
When 2013 arrived and Vail bought Mount Brighton, near Detroit, Michigan as part of its “Midwest urban strategy” to funnel regional skiers and snowboarders to Vail’s Western areas, he was tapped to overseeing the upgrading of that resort, where the company spent $10 million.
He stayed in Michigan for 2.5 years, taking over at Wilmot in early January. He jokes that he has found his “niche” in the company supervising do-overs at what he describes as “tired” resorts.
Ogilvie said Wilmot was launched nearly 80 years ago by Chicago architect Walter Stopa after Stopa “caught the skiing bug” on a trip to Europe. Over the years, Stopa installed lights for night skiing and built one of the country’s first primitive snowmaking systems.
Ogilivie said he hadn’t seen the resort for years until he returned in 2015 for a look.
“It’s been here for a long time and has great tradition, but it really needed some help in terms of renovation and capital improvements,” he said.
“I was amazed how it looked just the same as when I was a kid in the 90s. Nothing had changed other than the addition of a new tubing lodge that was built about five years ago.”
When I toured Wilmot with Ogilvie in early November to look at the improvements, the resort was a beehive of construction activity. Near the entrance, a pair of seemingly ancient snowcats were being loaded up for shipment to Oregon. The Riblet vehicles, used for grooming the slopes, dated to the 1970s and had seen decades of wear and tear.
Ogilview said Wilmot now has three new Doppelmayr “quad” chairs to zip skiers and snowboarders up the slopes, a completely renovated base area, 50 new snow guns and an expanded ski and snowboard school area – with part of a building dedicated specifically to children.
“People will recognize the hill, of course, and we kept the outline of the base building with its towers because we wanted to respect the tradition that was here. Generations of families have skied at Wilmot Mountain and loved it. But everything else, especially inside the buildings, will be drastically different and modernized. We’re pretty sure people will like that.”
Now settled into a home in Crystal Lake, not far from where he grew up, Ogilvie said he feels comfortable being back in the Midwest – even if the ski slopes aren’t as imposing as those in the Rockies.
“My kids have never had family nearby, so this is great,” he said. “My mom still lives in Lincolnshire, so it’s nice to have grandma around.”
For more information, see wilmotmountain.com. An unlimited adult season pass at Wilmot is $539, while an Epic Pass that allows unlimited access to Wilmot and skiing and snowboarding with some restrictions at other Vail resorts starts at $849 for an adult. Epic Passes must be purchased by Sunday(NOV. 20). For details, see
–By Brian E. Clark,