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Vail Pioneer Weekend is a fond reunion of people with a place they love

People gather for the Vail Pioneer Weekend dinner Saturday, Sept. 23, at Dobson Ice Arena in Vail. The event ran Thursday, Sept. 21, to Sunday, Sept. 24, in Vail.
Chris Dillmann | cdillmann@vaildaily.com |

VAIL — It was 2002 when Packy Walker, Josef Staufer and Joe Hanlon started a new Vail tradition: Pioneer Weekend. Since then, the weekend, held every five years, has become a celebration of Vail’s past and a way to honor those no longer among us.

This year’s Pioneer Weekend wraps up Sunday, Sept. 24, with a memorial at the Wedding Deck near Eagle’s Nest on Vail Mountain, followed by lunch. There, those who have gathered remember friends who have passed over the past five years. As time goes on, the list gets longer.

“I got the list the other day,” Walker said. “It’s three pages long.”



Diana Mathias was traveling last week, but said she hopes to attend the Sunday memorial. Mathias, who came to Vail in 1980, is Pioneer Weekend-eligible for the first time this year, when 1983-and-earlier arrivals were eligible to participate.

Mathias said she’s a little sad about missing the other weekend events. She’s heard from a lot of friends from those early days.

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“It’s so lovely to re-connect with old friends,” Mathias said. “So many people who have gone want to come back and see how (Vail) looks, and to re-connect. It’s like going back to college.”

Vail remains in their hearts

Brian Hall, the mastermind of the Beaver Creek Children’s Theater, is also Pioneer Weekend eligible this year for the first time. Hall has a previous commitment: His troupe is helping raise money for local elementary schools at the annual Wild West Day at 4 Eagle Ranch.

Hall echoed Mathias’ feeling that coming back to Vail is a bit like a class reunion.

Hall moved to Vail in 1981 with seven friends. Those friends, and four girlfriends, all lived in a two-bedroom apartment when they first arrived, which Hall recalled as a lot of fun, even if it could sometimes be a challenge to figure out where everyone would sleep on a given night.

Hall said he managed to stay in the Vail Valley. A lot of that original group didn’t.

“The place is beautiful, the people are wonderful,” Hall said. In those days, when someone left, it was usually to pursue an opportunity elsewhere.

“The people who left, left not because they wanted to, but because they had to,” Hall said. “There’s always a little bit of you left here.”

Walker was among the early Vail pioneers. He got to town in 1967, one year after Vail had become a town. The people in town then were especially close, he remembered.

“There were only 65 people here in those days,” Walker said, adding that in those days before Interstate 70, a six-hour round trip to Denver was the rule, not the exception.

“On days off, you spent it behind a steering wheel,” he said.

Still, Walker said, those days were “pretty romantic.” There was no TV, no radio, the only newspaper was the also-fledgling weekly newspaper, The Vail Trail.

“We looked forward to that every week,” Walker said.

Making time to talk

The Vail Chamber & Business Association is organizing this year’s celebration. Walker is happy about that — he can enjoy his weekend with old friends.

Chamber director Alison Wadey said the group’s board agreed because the event is great for the community.

“Most of the pioneers are still business owners,” Wadey said. “A lot of member businesses have helped grow the town.”

Wadey said a number of people have called to send their regrets.

“I had to make sure I had time to talk to them,” Wadey said. “They want to talk about how things were, and how they are. They want to reconnect and talk about the town they love.”

Of course, there have been a lot of changes in town, particularly in the past 15 years or so. When Wadey would tell callers about a cocktail reception at the Arrabelle at Vail Square, a number of people asked, “Where’s the Arrabelle?” Mentioning the side of the old gondola building in Lionshead Village was enough of a hint.

Wadey said this year’s memorial list will be the biggest so far, a function of the passage of time.

Walker said he’s looking forward to the memorial, but it will be hard to top the 2007 event.

That year’s memorial was led by Pastor Don Simonton — who’s on this year’s list. The Simonton family came to Vail in the 1960s, and Don was the first pastor at the fledgling chapel in town.

For the 2007 Pioneer weekend, Simonton was on the wedding deck. The sky was clear, and the leaves were in full color. During his remarks, a red-tailed hawk appeared over the deck and lingered.

“Everybody figured is was a spirit of someone,” Walker said.

This year, the Vail spirit will be at that deck, no matter the weather.

Vail Daily Business Editor Scott Miller can be reached at 970-748-2930, smiller@vaildaily.com and @scottnmiller.


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