Part of Ski to Sea’s culture is built on the wide range of its participants’ athleticism — anyone can join, but not everyone can win. Elite, sometimes Olympic-level athletes compete, as do those who showed up straight off their couch.
But those high-level athletes don’t all find the race the same way or participate for the same reasons. Some are Washington- or Whatcom County-based and have competed since they were teenagers; others are retired professionals who were recruited to aid a team’s quest to victory.
One thing is certain: The top end of the race is dominated by sponsored teams. Since 2009, a sponsored team has finished first in 11 of the 13 races.
In that same span, Boomer’s Drive-In has won the race three times — the most of any team. Even more impressive, those victories came in three straight years (2017–19). Birch Equipment and Barron Heating are the next closest teams with two race wins since 2009, and the former has won the last two.
Juan Castillo has been on the Boomer’s team since 2016 as its downhill runner. Castillo, 32, is a former Western Washington University track and field athlete who went on to compete at the 2017 USA Track and Field Senior Cross Country National Championships.
Castillo was recruited to the team, posting the second-fastest downhill run time in 2016 before earning the top time each of the next two years. In 2023, he was the fourth-fastest runner.
The incredible — and sometimes surprising — level of competition keeps Castillo coming back, in addition to his desire to remain an athlete post-college.
“I’ve always looked at it as, I mean, on paper, these guys are leaps and bounds ahead of me,” Castillo said. “But in a race like this, it’s anybody’s game if you play it right.”
His payment for helping bring three Ski to Sea titles to Boomer’s was burgers on the house.
“We get to eat food,” Castillo said, “which is fine with me because, at the end of the day, this is just for fun.”
Some sponsored teams, however, do invest more money into their recruited team members. Adam Loomis, a current multisport athlete and former member of the USA Nordic Combined Ski and Skimo (ski mountaineering) teams, raced with Birch Equipment last year and is returning in 2024.
Loomis, 32, posted the fastest downhill ski/snowboard leg time in 2023 by more than three minutes, helping propel Birch Equipment to its second straight race victory.
“It sounded like fun, so I said “Yeah, why not?’” Loomis said. “Skimo is such a small sport that there are only a few people in the country I know might be faster than me … I was optimistic that I could send the team off for the lead.”
Originally from Wisconsin and currently living in Park City, Utah, his travel and lodging are paid for. This year, Loomis will also have a rental car so he can further explore the region. Before last year, Seattle was the only city in Washington he had visited.
“[The race] is only a part of the weekend for me,” Loomis added. “The racing’s cool, but it’s getting to go up to what was, last year, a new place and a beautiful place — spend some time skiing in the backcountry there, do some running.”
Brian Gregg, originally from the Methow Valley and now living in Minneapolis, is another high-level cross-country skier who regularly competes in the race. Gregg, who competed in the 2014 Winter Olympics in Sochi, Russia, first began racing in Ski to Sea “around 2000” as a high schooler with his twin brother, Chad, and the pair still race to this day.
Gregg has also competed with Boomer’s Drive-In for the last three races and has won the cross-country ski leg each time. Gregg has won the leg in eight of the nine races he’s participated in since 2009.
“The race is part of us,” Gregg said. “It becomes a family tradition.”
Boomer’s will cover up to half of Gregg’s plane ticket to get to Bellingham. But Gregg used to have another motivation to participate: Each member of the winning team would get a free, round-trip ticket via a sponsorship from Alaska Airlines. Gregg used it to get to his professional competitions.
“That was pretty awesome,” Gregg said. “Because, you know, cross-country skiing is not a lucrative sport at all.”
But despite the presence of world-class athletes, Ski to Sea remains teeming with high-quality Whatcom County athletes, sponsored or not. The third-, fourth- and fifth-place finishers in 2023 all competed in the Whatcom County Open division, requiring all team members to be from the county.
Top women’s teams
Ski to Sea’s top women’s teams also remain mostly locally based.
Last year, the Sheroes finished second among all women’s teams, behind only BNP Realtors — a Whatcom County Women division team. The Sheroes finished first in the Competitive Women division, and 23rd overall.
The team’s downhill snowboarder, Alyson Carlyon Stewart, is a former Louisiana State University platform diver and current elite obstacle course racer. Carlyon Stewart, 39, and the Sheroes have mostly maintained the same team that began racing in Ski to Sea in 2013.
“We’re not a sponsored team. We’re just people who want to race and love the competitiveness of it,” she added. “I mean, we’re all competitive athletes, either actively or in college or at different times in our lives … the great thing about my team is everyone is so versatile.”
They have shuffled the legs they compete in multiple times. Carlyon Stewart has done the downhill run leg twice, posting the third-fastest women’s time in 2015. She was the fastest woman in the downhill ski/snowboard leg in 2018.
Connor J. Benintendi is a former CDN sports reporter, send tips and information to newstips@cascadiadaily.com.
