Dig in at Cowboy Dinner Tree

August 14, 2015 (Updated January 25, 2016)

It’s time to saddle up for a culinary adventure out of the Old West – a time when Oregon cowboys were a fixture of life across the high desert. Come along as we head to Oregon’s one and only Cowboy Dinner Tree!

When Oregon’s outback calls, you leave the tall timber and cascade mountain waterfalls behind and dive into a vast desert of sage and juniper. Head south of La Pine on State Highway 31 where the official Oregon Outback Scenic Byway takes the breath away at places like Fort Rock State Natural Area.

The Byway offers nearly two hundred miles of high desert landscape where distances are great, people are few and cowboy country comes to life. That is especially true near Silver Lake, where you will find the most entertaining chuck wagon – minus the wheels – where the staff is busy prepping for dinner guests.

“We are like the gateway to Southeastern Oregon,” said restaurant co-owner Jamie Roscoe, “If you take a map of Oregon and fold it on half, we’re right in the crease.”

His wife Angel quickly added, “Some people pull up, take a look and say, ‘I’m not sure that’s a restaurant!’ That’s what we want people to think – it is kind of a cozy shack and very cool.”

A giant juniper tree rises above the cozy building and a fence rail lined with saddles hint at what the rustic sign over the front entrance confirmed: you have arrived at the Cowboy Dinner Tree Restaurant where there are no strangers, just folks that owners Angel and Jamie Roscoe haven’t met yet.

“We offer a whole experience,” noted Jamie. “It’s not just about the amount of food we serve but it’s the quality of it, the atmosphere of the restaurant and the experience of old Oregon.”

The amount of food sets the dinner tree apart from just about anywhere else. Nearby, the Roscoes’ right hand man, Brian Baker, tends a gigantic barbeque with three distinct cooking chambers. Turns out, it was once a huge propane storage tank that’s been converted to outdoor cooking and giant sirloin steaks.

Baker smiled and said, “If they’ve been here before, they know what they are getting into and if not, their eyes get large and they usually say, ‘Whoa – I have to eat all of that?”

The sirloin steaks are 32 ounces each and are cooked to a delicious medium rare. The steak is one of just two entrees the Dinner Tree menu offers – the other is a whole 4-pound chicken.”We put the chickens on one hour before the guest’s reservation, so they cook for about an hour and twenty minutes,” noted the barbeque cook.

But it’s the steak dinner that has made the Cowboy Dinner Tree famous and has drawn hundreds of guests each weekend from across the country since 1992. Angel and Jamie bought the business from her mom three years ago and the couple continue to offer diners an Oregon cowboy experience. Just about everywhere you turn, there is a scene right out of the Old West.

The place is aptly described by Angel as “simply comfortable.” “Everything is homemade: the salads, dressing, two types of soup and homemade rolls and pink lemonade in a quart-sized mason jar. Our guests like the fact that we only offer two entrees – makes their dining decision easy – they know what we serve and they like that.”

The Cowboy Dinner Tree is open year-round by reservation only. They serve up to 500 steak dinners on a summer weekend, and by all accounts, the business thrives on a simple premise: large portions at a reasonable price.

And then there is the remoteness of the place. While some might grumble at the long drive, Angel said that most diners travel the distance because it takes some time to get there. “Sunsets out here are like nothing you’ve ever seen” said Angel.

About The

Grant McOmie
Grant McOmie is a Pacific Northwest broadcast journalist, teacher and author who writes and produces stories and special programs about the people, places, outdoor activities and environmental issues of the Pacific Northwest. A fifth generation Oregon native, Grant’s roots run deepest in the central Oregon region near Prineville and Redmond where his family continues to live.