Legacy Attractions: Flying W Ranch

Legacy Attractions: Flying W Ranch

There are few places in Colorado Springs that have as much iconic Wild West flair as the Flying W Ranch. For decades, the famous chuckwagon attraction has been serving up songs, stories and delicious down-home cooking to locals and visitors in the Pikes Peak region. It’s a place you can go and bring everyone in the family, from tiny toddlers and growing tweens, to teens, parents, grandparents and anyone else who wants to come along. It has everything you could want in a Colorado experience — live music with a cowboy theme, heaping plates of delicious food and a welcoming country atmosphere that will make you feel exactly like the family member you’ve just become.

Speaking of family, the center of this popular attraction is a family who has held fast to the traditions that make the ranch so special for the last 76 years. Four generations of Wolfes have contributed to the success of the Flying W Ranch, beginning with Marian, the daughter of original owner Don Wilson. Wilson sold three Kansas properties to launch his ranch in the Pikes Peak region in 1947 and invited his daughter and Russ Wolfe to join him on the adventure. In an acceptance speech for a Pikes Peak Range Riders Silver Spur award, Russ Wolfe shared his response to his father-in-law’s invite all those years ago, “I’ll do anything to get out of Kansas, especially if I can marry your daughter.” In the early years of the ranch, Wilson, his brother and his daughter and Russ raised Black Baldy cattle and champion quarter horses. 

They also supplemented the family income with paid trail rides on land that seemed to roll out forever around their home. Those paid trail rides, it turned out, would change the future of the Flying W forever. The lore of the ranch’s origin story is that these picturesque trail rides included a sort of potluck style meal that was extremely popular with visitors to the ranch. Riders would gather together surrounded by the breathtaking majesty of the Pikes Peak region and enjoy good food and better conversation. Then, a rather interesting change began to occur.

“In time, there were more people eating than riding,” says Leigh Ann Wolfe, a third-generation owner of the Flying W Ranch.” They got rid of the horses and went to cooking full time.” Wolfe says that the ranch eventually developed the Western Grounds for hosting the meals, describing the area as a “private Garden of the Gods-type wonderland.” In 1953, just six years after Wilson began hanging his hat west of the city of Colorado Springs, the chuckwagon dinners became official. As Wolfe so succinctly puts it, “The rest was history.” And oh boy does the ranch have plenty of that. 

The Flying W Wranglers Create Musical Magic in the Rockies

When the trail rides first began, music was a regular part of the dinners. Lots of folks dropped in to sing a song or two, but it wasn’t until 1957 that the ranch found its stars, the Flying W Wranglers. They were an instant hit with the crowds, singing the songs of the Old West and the life of a cowboy with heartfelt love and appreciation that resonated every time they took the stage. In addition to live music, the Wranglers also specialized in fun stories, gentle banter and family-friendly humor that still gets the crowd laughing to this day. At last count, more than 60 Wranglers have been a part of the crew, including the first female Wrangler, Cassy Weil, who was introduced to the world right before the grand reopening in 2020 (more on that in a moment). 

If you simply cannot get enough of those Flying W Wranglers, you’ll be delighted to know they have taken their old-school music into the modern age with on-demand streaming via Spotify. You can cue up your favorite cowboy jams in the car, at home or anywhere else you want to hear the harmony. There isn’t a huge selection, but there’s enough to wet your whistle, as the cowboys say. Despite being quite popular far beyond the borders of Colorado, the Flying W Wranglers have not spent a lot of time recording tons of new albums — not even when they had their own recording studio located on the property. It’s hard to find time when you’re performing for adoring fans on a near-nightly basis.

That’s not to say the Wranglers have never left the farm. To the contrary, they’ve been seasoned travelers throughout the years, According to the Flying W Ranch, the cowboys have been all over the world, including providing entertainment to the troops as part of the USO during the Vietnam War, performing at the Grand Ole Opry in Nashville, and making appearances in London, D.C., and New York City. They are known for old cowboy tunes, poignant gospel tracks and a powerful rendition of the National Anthem all sung in beautiful harmony. To date, they are the second oldest western performance band on earth (but forever the number one favorite in the hearts of Coloradans). 

The Fire and the Phoenix: Flying W Rises from Literal Ashes

Like many local area attractions, the Flying W Ranch has also experienced its share of terrible hardships in its 76 years in business. One of the most devastating challenges was the complete destruction of the ranch during the infamous Waldo Canyon fire that ravaged Colorado Springs in 2012. All but one structure on the property — a place that had served visiting families for nearly six decades at the time of the fire — were completely destroyed. For the Wolfe family, an entire legacy lay seemingly in ruins. Then came the floods. 

Wildfires don’t just destroy the plants and trees that help absorb rainfall and runoff. They also damage the ground itself. The heat of a wildfire chars the ground and seals it, making it impossible for falling water to absorb into the soil. That water either collects where it falls, or begins to travel the path of least resistance. In the case of the Flying W, that water found its way down into the property in the year following the Waldo Canyon fire. The family still refused to give up. 

It would take several more years — 8 for those counting — for the recovery efforts to succeed. In a story by the Colorado Springs Gazette, Wolfe explained that volunteers and neighbors excavated 13 giant debris basins to protect the property and donated 114,000 cubic yards of gravel to the city of Colorado Springs as part of their mitigation strategy. Finally, in 2020, the ranch was able to host guests, albeit for a rather short season due to the global pandemic. Nonetheless, the ranch was finally back in business serving up beans, cornbread and community for guests from all over the world. It is the cowboy way, after all. 

Soaring into the Future

While the fire is certainly a dramatic moment in Flying W history, it hardly casts a shadow over the joy and community the ranch has created over 7 decades of operation. Wolfe and the Flying W Ranch crew are far more interested in the joy they have provided to millions of families through seven decades of devotion to their attraction. It is one of the top places to visit in the Pikes Peak region, drawing visitors from all over the world and even a fair number of celebrities. 

Flying W is mostly mum about celebrity visits to protect guest privacy and ensure famous folks can feel safe bringing their families. Wolfe does note that there are “too many to count.” However, she did share that the Shah of Iran, Mohammad Reza Pahlavi, once visited in the late 1960s and complimented her “pretty green eyes” as she served him and the other guests lemonade. When it comes to name dropping, meeting the last king of the now-abolished Iranian monarchy at a chuckwagon supper in the United States is definitely a good one. 

Asked what makes the Flying W so very special to visitors, Wolfe says, “We keep the Old West alive. Generations of families return year after year to the Colorado Springs region with the sole purpose of visiting the Flying W Ranch. People from 3 to 93 say it is the highlight of their visit to Colorado.” As you might imagine, that makes the Flying W Ranch pretty special to the Pikes Peak region. At last count, the ranch has welcomed more than 8.5 million visitors, many of whom, as Wolfe just pointed out, are repeat visitors bringing new generations of their family to join in on the tradition. “We have been a “Yellowstone” from the start,” says Wolfe, “the only difference being that we are the real deal.”