May 2026 marks the tenth anniversary of the High Horse Saloon & Eatery at 3953 Montana Avenue in Billings.

By all measures this entrepreneurial challenge of Reid Pyburn is a huge success. From morning till night, most days are dynamically busy. Guests come for the hearty meals, to visit with friends over a beer, relax for a while in the casino, to participate in bingo or enjoy music and dancing. They come, and then come again and again.

There are mornings, on the weekend, that hungry patrons will wait for more than an hour to enjoy breakfast at the High Horse – it is just that busy! Even when anxious staff, emerge to explain that there is a long wait, very few patrons leave. They came to have breakfast at the High Horse and that’s what they are going to do!

This success is what the High Horse will be celebrating throughout the month of May. Many events will happening in May, but the one consistency will be that every day every beef entre will be ten percent off steak and prime rib dinners, as a thank you to patrons.

Asked what brings people to the High Horse, Pyburn said, it’s no one thing that draws them, it’s the “experience,” which he attributes to the staff. If he has any role in making it happen, it is in getting and keeping good personnel, said Pyburn. They help create a culture that people enjoy.  They work hard to make sure that the food is good, the service is prompt and friendly, that the experience is great.

It’s hard to believe that ten years have passed. Much has happened during those ten years, including some real challenges. In looking back, Pyburn sees that it was the challenges that have contributed to their success. They had to come up with innovative ideas that met the immediate need, but it was that creativity that put them on the map.

Of course, in the midst of it all, Pyburn married well. His wife, Shawna, has contributed a lot of hard work and innovation, to the business. Her contribution to the enterprise allowed for the expansion of the business, with the acquisition a few years ago of The Squire Lounge, an historic Billings business, on Broadwater Avenue.

Shawna’s responsibilities fall into the realm of bookkeeping, organizing, and dealing with issues that impact the almost 100 employees that are employed at the High Horse and the Squire. She plans special events and oversees catering. She also makes great desserts.

Pyburn, who worked since his teen years at The Rex in downtown Billings, learned a lot from a generous employer, Gene Burgad, who gave him every opportunity to learn the ropes, from bus boy and server, to bartender and eventually, manager. But when the Rex closed, Pyburn found himself looking for an opportunity.

The High Horse wasn’t a dream, it was an “opportunity.” While Pyburn “knew food,” he was thinking more along the lines of someday owning a “honkytonk,” but the high cost of a liquor license loomed as a significant barrier.

The High Horse was an opportunity brought to him by Jim Kisling, a local contractor and former patron of The Rex, who Pyburn had come to know. Kisling bought the former Montana Chads and “put it all together,” and then offered Pyburn an owner-manager partnership. “My job was to make it work. To be flexible and adapt to whatever came up. About the time we figured it out, COVID happened and then it was like a restart,” said Pyburn.

Pyburn readily embraced Kisling’s proposal, still envisioning a honkytonk. The emergence of the High Horse as a premier steak house was due to the impact of the COVID crisis, under which many businesses – especially restaurants — were forced to close. Together, Reid and Shawna strategized on how to continue in business under the government restraints.

With so many restaurants closed, “take out” became the only alternative for those who didn’t want to cook. Pizza was the primary option, but even pizza can become tiresome. The High Horse started offering “take out” prime rib dinners, which patrons could pick up in late afternoon. Word spread quickly and most days saw lines of people extending out into the parking lot at 5 pm, waiting to pick up their prime rib dinner.

That’s what put the High Horse on the map for many folks in Billings, and pushed it irretrievably into the category of “restaurant.” “It’s still a honkytonk,” Pyburn can be heard to mumble, who enjoys getting to know his customers and planning events and entertainment for the neighborhood and community.

Takeout prime rib was just one of the things the Pyburns did to stay in business during the tough days of COVID. They embraced maintenance projects, for which they called upon staff to help, which kept them in touch with staff, as well as offering them a means of earning some extra income.

Prime rib remains on the menu for breakfast, lunch and dinner. One of Pyburn’s early commitments was making Montana beef the basis of the menu. It is a salute to his heritage of growing up in an agriculture community, as well as to the cattle industry which is foundational to the community and economy.

Pyburn partnered with Certified Angus Beef and local producers to build a menu that featured the best of beef, locally produced – steaks as well as prime rib. (Yes, there is some chicken on the menu.) Most of the beef came from bulls sold through Pat Goggins’ Livestock Auction Yard, muses Pyburn in pondering the past; but, it all comes from Montana ranchers.

As the High Horse thrived, gradually Pyburn was able to buy out Kisling’s investment in the business. Today the Pyburns move into their next decade as full owners of the High Horse.

As the High Horses popularity grew so did requests for catering. Catering became a third enterprise, pushing them to purchase an off -site kitchen. Most recently, the Pyburns sold the catering business to the High Horse’s first chef, Andy Glynn and his wife, Rachel, who also worked several years in the catering part of the High Horse business. The Glynns have launched their own business, Timber and Thyme, which still functions cooperatively with the High Horse.

Having grown up as part of the Billings restaurant community, Pyburn knows many in the business, which has been a huge benefit in getting great employees. He worked with many of them at The Rex. That’s where he first got to know the Tyler Ellis, who today is General Manager at the High Horse.

Then there is Karla Ferguson, who began working at The Rex in 1988. She was there the first day Pyburn became a busboy. Today she is one of High Horses’ best waitresses, as well as a good friend.

Three of the waitresses have been at the High Horse since its very first day: Ronda Buerkley, Angie Warren, and Sarah Ellis. They are part of a cadre of many others who have been with the High Horses for many of its ten years. Getting to know them is much of the enjoyment of the High Horse.

steak and prime rib dinners, as a thank you to patrons.

Asked what brings people to the High Horse, Pyburn said, it’s no one thing that draws them, it’s the “experience,” which he attributes to the staff. If he has any role in making it happen, it is in getting and keeping good personnel, said Pyburn. They help create a culture that people enjoy.  They work hard to make sure that the food is good, the service is prompt and friendly, that the experience is great.

It’s hard to believe that ten years have passed. Much has happened during those ten years, including some real challenges. In looking back, Pyburn sees that it was the challenges that have contributed to their success. They had to come up with innovative ideas that met the immediate need, but it was that creativity that put them on the map.

Of course, in the midst of it all, Pyburn married well. His wife, Shawna, has contributed a lot of hard work and innovation, to the business. Her contribution to the enterprise allowed for the expansion of the business, with the acquisition a few years ago of The Squire Lounge, an historic Billings business, on Broadwater Avenue.

Shawna’s responsibilities fall into the realm of bookkeeping, organizing, and dealing with issues that impact the almost 100 employees that are employed at the High Horse and the Squire. She plans special events and oversees catering. She also makes great desserts.

Pyburn, who worked since his teen years at The Rex in downtown Billings, learned a lot from a generous employer, Gene Burgad, who gave him every opportunity to learn the ropes, from bus boy and server, to bartender and eventually, manager. But when the Rex closed, Pyburn found himself looking for an opportunity.

The High Horse wasn’t a dream, it was an “opportunity.” While Pyburn “knew food,” he was thinking more along the lines of someday owning a “honkytonk,” but the high cost of a liquor license loomed as a significant barrier.

The High Horse was an opportunity brought to him by Jim Kisling, a local contractor and former patron of The Rex, who Pyburn had come to know. Kisling bought the former Montana Chads and “put it all together,” and then offered Pyburn an owner-manager partnership. “My job was to make it work. To be flexible and adapt to whatever came up. About the time we figured it out, COVID happened and then it was like a restart,” said Pyburn.

Pyburn readily embraced Kisling’s proposal, still envisioning a honkytonk. The emergence of the High Horse as a premier steak house was due to the impact of the COVID crisis, under which many businesses – especially restaurants — were forced to close. Together, Reid and Shawna strategized on how to continue in business under the government restraints.

With so many restaurants closed, “take out” became the only alternative for those who didn’t want to cook. Pizza was the primary option, but even pizza can become tiresome. The High Horse started offering “take out” prime rib dinners, which patrons could pick up in late afternoon. Word spread quickly and most days saw lines of people extending out into the parking lot at 5 pm, waiting to pick up their prime rib dinner.

That’s what put the High Horse on the map for many folks in Billings, and pushed it irretrievably into the category of “restaurant.” “It’s still a honkytonk,” Pyburn can be heard to mumble, who enjoys getting to know his customers and planning events and entertainment for the neighborhood and community.

Takeout prime rib was just one of the things the Pyburns did to stay in business during the tough days of COVID. They embraced maintenance projects, for which they called upon staff to help, which kept them in touch with staff, as well as offering them a means of earning some extra income.

Prime rib remains on the menu for breakfast, lunch and dinner. One of Pyburn’s early commitments was making Montana beef the basis of the menu. It is a salute to his heritage of growing up in an agriculture community, as well as to the cattle industry which is foundational to the community and economy.

Pyburn partnered with Certified Angus Beef and local producers to build a menu that featured the best of beef, locally produced – steaks as well as prime rib. (Yes, there is some chicken on the menu.) Most of the beef came from bulls sold through Pat Goggins’ Livestock Auction Yard, muses Pyburn in pondering the past; but, it all comes from Montana ranchers.

As the High Horse thrived, gradually Pyburn was able to buy out Kisling’s investment in the business. Today the Pyburns move into their next decade as full owners of the High Horse.

As the High Horses popularity grew so did requests for catering. Catering became a third enterprise, pushing them to purchase an off -site kitchen. Most recently, the Pyburns sold the catering business to the High Horse’s first chef, Andy Glynn and his wife, Rachel, who also worked several years in the catering part of the High Horse business. The Glynns have launched their own business, Timber and Thyme, which still functions cooperatively with the High Horse.

Having grown up as part of the Billings restaurant community, Pyburn knows many in the business, which has been a huge benefit in getting great employees. He worked with many of them at The Rex. That’s where he first got to know the Tyler Ellis, who today is General Manager at the High Horse.

Then there is Karla Ferguson, who began working at The Rex in 1988. She was there the first day Pyburn became a busboy. Today she is one of High Horses’ best waitresses, as well as a good friend.

Three of the waitresses have been at the High Horse since its very first day: Ronda Buerkley, Angie Warren, and Sarah Ellis. They are part of a cadre of many others who have been with the High Horses for many of its ten years. Getting to know them is much of the enjoyment of the High Horse.