Stars, Steaks, and Strange Brews

Forget Michelin stars. Deep in Oregon's high desert, legendary Cowboy Dinner Tree is destination dining at its most deliciously down-to-earth, well worth the required reservation and scenic drive from Bend (about 90 minutes) or Klamath Falls (roughly two and a half hours).

The journey is part of the experience, following quiet roads through wide-open sagebrush country. There's no grand entrance announcing your arrival, just a modest sign pointing you in the general direction. (You'll get there.) The off-the-grid setting has an unpretentious appeal and some cowboy lore to match. As the story goes, cattle drivers along the Sycan Trail once stopped beneath a big juniper tree for a chuck-wagon meal of beans and biscuits. Those cowboys have long since ridden off, but the dinner tradition lives on. Jamie and Angel Roscoe, along with their children, keep it all in the family.

Forget white linens. Natural wood tables fill a cozy, low-ceilinged, three-room hideaway decked out in Western memorabilia. Dollar bills left by diners paper the walls and ceiling, but they're more than décor. The Roscoe family collects them and puts the money toward good causes, from helping local families to supporting charities.

Giddyup! It's time for a frontier feast. Fresh-baked sweet yeast rolls (ask about extras when you reserve), salad, hearty soup (pro tip: ask ahead about the corn chowder), and a choice of two entrées. There's the famous Cowboy Cut, a nearly two-pound top sirloin steak that makes the giant baked potato beside it look small. (It's an optical illusion. The potato's big, too.) Prefer chicken? That'll be an entire roasted bird … the whole clucking thing.

Coffee, iced tea, and pink lemonade are the drinks on offer, and homemade dessert rounds out the meal. Yes, to-go boxes are provided. And yes, you're gonna need one. Don't try to be a hero, cowboy!

When you finally push back from the table, step outside and look up. Depending on your dinner time and the season, you might catch the setting sun casting golden bands across the sagebrush—or a sky full of stars blazing across the dark desert.

Before you ride off into the sunset (or starlight), stop at the gift shop. At the very least, you'll want a coffee mug or a koozie to remember this one.

Cowboy Dinner Tree gets all the stars!

TIP: Reservations are required, and Cowboy Dinner Tree accepts cash only. Book well ahead and check seasonal operating days before making the drive.

Make a Night of It: After a cowboy-sized feast, you may want to keep your commute short. Ask Cowboy Dinner Tree about its on-site cabins (their lodging page has plenty of other lodging recommendations nearby, too). There's also The Lodge at Summer Lake for rustic digs and more high-desert scenery, as well as Summer Lake Hot Springs in Paisley, where an overnight stay comes with the chance for a geothermal soak. Your reward? A little more time under those big Oregon skies.

TIP: Check out this 7-Day Road Trip to Cowboy Dinner Tree.

Back in Bend: A Very "Worthy" Destination!

The new rock stars? The ones living on the third rock from the sun! They know what's up when the lights go down. Just ask Grant Tandy, astronomer and NASA-JPL Solar System Ambassador at Bend's Worthy Brewing Hopservatory.

Worthy Brewing takes stargazing to new levels. Specifically, level three, where the Hopservatory awaits. But first, settle in for some stellar brews and bites inside the brewery or on its spacious outdoor patio, warmed by heat lamps and fire pits. Pair a wood-fired pizza with a hop-forward beer like the Worthy Oregon IPA.

Later, take the winding stairs or elevator up to the Hopservatory, a dome that's home to a 16-inch research-grade telescope. There's no admission fee, though a $5 donation is suggested. When Grant's on duty, drop by, say hi, and ask what's up. Because he'll show you what's up!

As the dome opens and Grant trains the telescope on the night sky, celestial celebrities come into focus—from Vega, one of the brightest stars in the sky, to Saturn and its spectacular rings, or Jupiter and its moons when they're in view. Now that's a star-studded lineup.

CAMPFIRE HOTEL: For a Bend basecamp with retro flair, check into the Campfire Hotel. Vintage vibes meet modern comforts, and at night everything is warmly lit, from the ambient lights around the property to the glowing fire pit where everyone gathers for some fireside s’mores (get a s’mores kit in the lobby). Yum.

Sink into the year-round saltwater pool and hot tub (you might just leave as Pool Club VIP). The lobby is stocked with quirky, cool finds, including artisan souvenirs like soap and all kinds of stylish stickers.

Start your morning with some tasty coffee and a hearty breakfast from Burrito Sunrise, the rise-and-shine yellow food truck on-site.