As we head into a brand-new year, more Oregonians are thinking less about resolutions and more about experiences. The kind you do not scroll past and forget, but actually remember years later. If 2026 is the year you finally stop saying someday and start saying let’s go, there is one place in Oregon that belongs at the very top of your bucket list.
It sits far from freeways, traffic, and cell service. There is no marquee sign, no polished exterior, and no hint that one of the state’s most unforgettable meals waits inside. And yet, for decades, people have willingly driven deep into Oregon’s high desert for one reason only.
Dinner.
The Cowboy Dinner Tree, tucked outside the tiny outback community of Silver Lake about 90 minutes southeast of Bend, is unlike anywhere else in Oregon. At first glance, many people do not even realize it is a restaurant at all. It looks more like a weathered homestead than a place serving legendary meals, and that is exactly the appeal.
Long before it ever became a restaurant, the building was a homestead constructed in the late 1800s and later used for storage. But the land itself has been feeding people for far longer. In the late 19th century, ranchers driving cattle from Silver Lake toward the Sycan Marsh would stop near a massive juniper tree that marked the halfway point of the trail. Beneath that tree sat a chuckwagon where tired cowboys were served heaping portions of beans and biscuits before continuing on their journey.
That same juniper tree still stands today just behind the back entrance of the restaurant, a quiet reminder that this spot has always been about filling hungry travelers before they move on.
The Cowboy Dinner Tree officially became a restaurant in 1992, and today it is run by Jamie and Angel Roscoe, who have carefully preserved the spirit that made the place legendary in the first place. There is no rush here, no pretension, and no attempt to modernize what already works.
The menu is famously simple. There are only two entrées to choose from: a whole roasted chicken or a massive 26 to 30 ounce steak. That is it. And somehow, it is more than enough.
Every meal comes with bottomless beans, bottomless salad, and fresh homemade rolls, all made from scratch. Portions are generous in a way that feels almost unheard of now, and no one leaves hungry. Dessert is classic comfort food, with berry shortcake being a favorite, and the pink lemonade has become something of a local legend. Coffee and iced tea round out the experience, keeping things simple and familiar.
The cost is $45 per person, with kids six and under eating free and children ages seven to thirteen costing just $11. If there is one piece of advice nearly every guest gives, it is this: bring a cooler. Leftovers are not just common. They are expected.
One of the most surprising parts of the experience is that you do not actually have to leave once dinner is over. If you are not ready to drive back into the dark open high desert, the Cowboy Dinner Tree rents out rustic wood stove heated cabins for the night. They are simple, cozy, and perfectly on theme, complete with electricity, a shower, and even an old school Mr. Coffee waiting for you in the morning. It feels less like booking a stay and more like stepping back into another era.
There are a few important things to know before you go. Reservations are required, and the Cowboy Dinner Tree is cash only. No cards and no exceptions. Dinner is served every half hour from 4:00 p.m. to 7:30 p.m., and hours vary by season. From December 1 through January 31, they are open Saturdays only. In February, they open Fridays and Saturdays. From March through the Sunday before Memorial Day, they are open Fridays, Saturdays, and Sundays. From Memorial Day weekend through October 31, they are open Thursday through Sunday. November returns to a Friday through Sunday schedule.
To reserve a spot, you will need to call 541-576-2426.
Getting there is part of the adventure. From Bend, drive south on U.S. 97 for 31 miles, turn left onto Oregon 31 South, and continue for 47 miles. Turn right onto East Bay Road and drive 4.2 miles. The Cowboy Dinner Tree sits about 5.1 miles south of Silver Lake, roughly a 45 minute drive from Fort Rock.
Oregon has no shortage of great food, but places like this are becoming rare. Restaurants where the menu has not changed because it does not need to. Places where dinner feels like an event instead of a transaction. Places that still require a phone call, a reservation, and a little effort to reach.
As we roll into 2026, the Cowboy Dinner Tree feels less like a restaurant and more like a reminder. Some of Oregon’s best experiences still live far off the beaten path, and they are worth every mile it takes to get there.
If you are building your 2026 Oregon bucket list, this is one trip you will not regret making.
