Finger pushing


Flying W Ranch: A western tradition triumphs over tragedy in Colorado Springs

The crowd has moved through the line, filling trays with chicken, brisket, potatoes, beans, biscuits and applesauce made just the way an adoring mother made it more than 70 years ago.

Now the people are back at their seats, back at the picnic tables lining this dining hall at a historic ranch in Colorado Springs, where horses and cattle roam between green hills, red rock cathedrals and trickling streams, where the sun sets behind the mountains and the city twinkles in view.

The Flying W Wranglers take the stage, cowboy hats and fiddle and all.

The Flying W Wranglers play for guests following a Chuckwagon Supper June 20, 2026 at Flying W Ranch. Photo by Mark Reis
The Flying W Wranglers play for guests following a Chuckwagon Supper June 20, 2026 at Flying W Ranch. Photo by Mark Reis

“I wanna smell the Western air, from the back of a chestnut mare,” they start, the five of them in harmony.

The crowd sways as the voices rise. “Let me never wander from my Colorado home …”

For generations, local regulars and tourists alike have found home at Flying W Ranch’s Chuckwagon Dinner Shows.

What is it that has kept people coming back since 1953?

“The romance of the Old West, it’s always been there,” says Leigh Ann Wolfe, who continues the tradition her parents started.

“It’s a trip down memory lane,” says her son, Hutch, representing the fourth generation of the Flying W family. “The world’s going crazy, and this isn’t going crazy yet.”

Evelyn Kraut of Colorado Springs plays next to a pond before heading to the Chuckwagon Supper at The Flying W Ranch June 20, 2026. Photo by Mark Reis
Evelyn Kraut of Colorado Springs plays next to a pond before heading to the Chuckwagon Supper at The Flying W Ranch June 20, 2026. Photo by Mark Reis

However idyllic, however seemingly protected and frozen in time, the whims of the world have left their mark on the ranch.

In view is the scorched ridge from which the flames came in 2012. The Waldo Canyon fire destroyed the place Leigh Ann’s parents built.

Ever since she embarked on a multimillion-dollar rebuild and welcomed back guests in 2020, she has heard how beautiful it all is. How the fire had a way of clearing trees and opening a scene similar to the nearby Garden of the Gods. That’s not how Leigh Ann sees it.

“It was the most beautiful ranch in the state of Colorado,” she says. “This is not even 10% of what it used to be.”

Sometimes it’s hard for her to look out at it ー the pines gone along with the dozens of structures resembling an Old West village, her father’s life’s work.

Work remains hard for Leigh Ann approaching 70. She’s still raising horses and cattle like her grandparents and parents before her, still serving food many nights and running dishes alongside Hutch and her daughter, Ruth.

The show happens every night of the summer, but “it’s an all-day thing,” Ruth says.

And she’ll be here all day if she has to. “It’s a blessing what we do,” she says.

It is as the family’s faith has always mandated: “to be a blessing to others,” Leigh Ann says. “To whom much is given, much is expected, and that’s really what I live my life on. I think (God) expects a lot of me, because I got to live in this very ideal situation growing up as a kid.”

Leigh Ann Wolfe serves up extras to the plate of a young diner at the Chuckwagon Supper at The Flying W Ranch June 20, 2026. Photo by Mark Reis
Leigh Ann Wolfe serves up extras to the plate of a young diner at the Chuckwagon Supper at The Flying W Ranch June 20, 2026. Photo by Mark Reis

Leigh Ann grew up in the early years of the Flying W Chuckwagon Suppers and Original Western Stage Show, as it came to be billed.

It all started here where Don Wilson moved his family in 1947, swapping the ranch in Kansas for this land once owned by Colorado Springs founder Gen. William Jackson Palmer. Wilson would raise champion quarter horses and Hereford bulls. His daughter, Marian, and her high school sweetheart, Russ Wolfe, would run the ranch upon Russ’ return from World War II.

Along with the horses and cattle, Russ and Marian raised a family. Leigh Ann was born in 1956.

“They needed money in those early years,” she says. They saw an opportunity in the horseback rides that Russ led, ending with a home-cooked meal from Marian.

Starting in 1957, the Flying W Wranglers attracted new crowds. From nightly guests counted on one or two hands at the beginning, the Chuckwagon now hosts tens of thousands every summer.

The ranch maintains a story from Russ: “In time, there were still 20 horses but 400 people for dinner. Then there were 20 horses and 800 people for dinner, and then 20 horses and 1,000 people. We finally just got rid of the horses.”

He was mostly joking. Even as Russ spent decades building the trading post, drugstore, train depot, church and schoolhouse among nearly 30 buildings for his Western village, the family never abandoned horses and an old way of life.

Cash Villers from Brighton greets Flying W Ranch employees Duke Pingrey and Sophia Bailey as they sit atop their horses at the ranch June 20, 2026. Photo by Mark Reis
Cash Villers from Brighton greets Flying W Ranch employees Duke Pingrey and Sophia Bailey as they sit atop their horses at the ranch June 20, 2026. Photo by Mark Reis

“It’s just what we did,” Leigh Ann says. “I wasn’t your typical kid. I worked all the time. From when I could walk, I was serving lemonade.”

Her life took a rather drastic turn to New York City. Out of business school, she spent a decade trading foreign exchange on Wall Street. Later, she and her husband grew a successful business selling software to large companies.

“We actually were in the process of selling it just before the fire,” Leigh Ann says.

The 2012 fire changed any ideas she had for a slower life. She returned to the ranch, the beautiful green having been replaced by black with ash and rubble. Perhaps mercifully, Leigh Ann’s mother wasn’t around to see it. Her father was nearing the end of a struggle with dementia that could not hide his pain.

“Everything they did, and it was just gone in the blink of an eye,” Leigh Ann says.

Maybe, after all, she would go study art or slow down in some other way. Amid the wreckage, she could not imagine a future here.

“My daughter was really the one who said, ‘Mom, we gotta do this,’” Leigh Ann recalls. “‘If we fail, we fail. But we’ve got to try. The legacy is too deep.’”

Guests ride in a wagon pulled by two Percherons at The Flying W Ranch June 20, 2026. Photo by Mark Reis
Guests ride in a wagon pulled by two Percherons at The Flying W Ranch June 20, 2026. Photo by Mark Reis

And so the family went to work, taking money from the sale of the software business and pouring it into the new venue and other infrastructure. Along with permitting and insurance hassles, more attention went to highly technical environmental restoration and mitigation.

All the while, Leigh Ann wondered, would people even want to come back? “It was misery,” she says.

One thing still stood on the ranch, somehow: a charred cross, reminding of her faith. She had other reminders, including a poem from her grandfather.

“You are never alone, you know,” Don Wilson wrote in the ranch’s early years. “When sorrow comes your way, many others’ thoughts and prayers are with you all the way.”

That much was clear at the reopening in 2020. The people indeed came back, despite the loss of Old West buildings and trees.

Maybe more buildings will return someday, along with the pines. Leigh Ann has hope: “My kids will see some trees in their lifetime.”

As will generations of local regulars and tourists to come. Today, they come for a show that features a tribute to a family’s history.

Leigh Ann stops to watch between running dishes. “I always tear up in the back,” she says.

On the big screen behind the stage, pictures flash of her grandparents and parents while the band sings. “I’m a whispering wind in the trees now …”

There’s Leigh Ann as a kid. There she is with her own kids, Hutch and Ruth. The pictures continue with the song.

“When you pass on, what you gonna pass down …”

And then the last picture: Leigh Ann and the kids with their arms wrapped around each other, walking out to the ranch forever changed, forever home.



Welcome Back.

Streak: 9 days i

Stories you've missed since your last login:

Stories you've saved for later:

Recommended stories based on your interests:

Edit my interests