Aspen Gay Ski Week downhill event has evolved into connection with community |

Aspen Gay Ski Week downhill event has evolved into connection with community

Erica Robbie
The Aspen Times


For tickets and more information, visit

--Lunch at the Sundeck, Aspen Mountain, 12:30 to 2 p.m.

--“Friendship dinner” at Element 47 at The Little Nell, 6 to 10 p.m.

--“Big Gay Ice Show” at Aspen Recreation Center, 7:15 to 8:15 p.m. Olympic skaters will perform.

--Pool party at Aspen Recreation Center, 8:30 p.m. to 1:30 a.m. South Beach theme.


1st: Snowmass Tourism

2nd: Aspen Skiing Co.

3rd: Scott Graham

During the early years of Gay Ski Week, a gaggle of men would dress in drag and ski like hell down the once mogul-ridden Ruthie’s Run on Aspen Mountain.

Chilled libations in hand, spectators would soak in the scene from the patio of the now-defunct Ruthie’s Restaurant at the bottom of the run, recalled Bruce Lee, one of the founders of the 42-year-old Aspen Gay Ski Week.

Gay Ski Week attendees chose Ruthie’s as the course because of its “big, nasty bumps,” Lee said this week during a break in the festivities.

“We didn’t even tell (the Ruthie’s Restaurant staff) the first year, we just showed up and the guys at the restaurant made a fortune and they said, ‘Hey, we love you guys, come back next year.’”

Today, this episode is known as the annual downhill costume competition, one of the most anticipated events throughout the weeklong celebration.

On Friday, a few hundred people gathered at the base of Aspen Mountain to watch costume-clad teams and individuals glide down the slopes amid a colorful and snowy scene.

For Gay Ski Week organizers and participants, the downhill costume contest also is special in that it is among the few events that integrate the local and LGBTQ communities.

“I feel like it is the one event during (Gay) Ski Week that brings the participants and the city of Aspen together because the city people turn out for this,” said Paul J. Williams, whose drag character, Sister Helen Holy, serves as the contest’s beloved emcee.

“When I can get positive feedback from (Gay Ski Week) participants, as well as locals who are not even a part of the LGBT community — that is gratifying,” Williams said. “And that is building bridges that make me happy.”

Equal parts satire and wit, Sister Helen Holy is a result of Williams’ upbringing in the Southern Baptist Church.

Having led the costume contest as emcee since 2001 (with the exception of a brief and recent stint in which Logo TV sponsored Gay Ski Week), Sister Helen Holy is now part of the fabric of the event.

Over the years, she’s witnessed the event’s evolution into a more polished production, much of which she credits to event director Pamela Herr.

“I personally was very skeptical of a straight woman coming in and taking over this fabulous gay event,” Williams quipped, “but she has been a godsend.”

“Each year, they sell more tables, which only brings in more income for (Aspen OUT),” “Helen” added. AspenOUT is the nonprofit that produces Gay Ski Week and donates 100 percent of the proceeds to LBTGQ causes locally and nationally.

Tables for this year’s downhill event sold out.

As part of the costume contest each year, a panel of eight or so judges rank the contestants.

One of those judges is Pitkin County Sheriff Joe DiSalvo, who’s become a mainstay of the downhill event.

DiSalvo said he adds the event to his calendar about a year in advance.

“This is a special event for me. I think it’s unique, and I think it’s something a lot of towns and communities should do more of,” DiSalvo said. “I support a lot of local events, but this is one of my favorites.”