Oregon Trip Planner: Sisters

The Three Sisters loom over Sisters.

Plan a Trip to Sisters, Oregon

written by Kevin Max

Sometime in the 1970s, late poet laureate, William Stafford, described his move to his coveted Sisters in the following verse:

When we first moved here, pulled
the trees in around us, curled
our backs to the wind, no one
had ever hit the moon—no one …
This message we smuggle out in
its plain cover, to be opened
quietly: Friends everywhere—
we are alive! Those moon rockets
have missed millions of secret
places! Best wishes.
Burn this.

Stafford would have looked southwest and seen the snow-capped Three Sisters, brilliant bulbs in the blue sky. He would have seen the pointy peak of Mt. Washington almost directly west and the perfect cone of Black Butte to the northwest. At his feet, hundreds of acres of good horse rangeland. All of this, secret places that moon rockets missed.

Only a few hundred people called Sisters home at that time. Logging had come and gone. Lots at nearby Black Butte Ranch had just begun selling in 1970. The first Sisters Outdoor Quilt Show—now a bustling international “who’s who” of quilting—unfolded itself up the sides of the few buildings in the stamp-sized downtown. The Western-themed zoning ordinance took root. The community of Sisters had just started its journey.

The law of small numbers aside, consider that Sisters’ population has doubled over the past ten years to 2,055. Even though Sisters is a tourism-driven economy, surpassing the 2,000 mark in year-round population means its shops are a little more viable, the restaurants serve a full menu during the week and the FivePine Lodge campus is pumping with residents who sent their own letters of domestic glee ending with Stafford’s instructions, Burn this.


Oregon Trip Planner Day One: Cabins | Brews | Motion Pics


The first day usually means you’ve driven a good distance from somewhere else. It also is likely that, to get there, you’ve surfed over a mountain pass with snow as white as your knuckles. When you’ve put in that kind of nerve on the road, sometimes the best thing is just to find a cozy spot with a glass of wine or a pint of beer, and grab a book or see a movie you’ve been too busy to make.

The FivePine Lodge on the east end of Sisters is part of a larger walking campus that can neatly accommodate all of those needs and more. And, thankfully, you don’t have to get behind the wheel again.

The twenty-four cabins are tucked into the edge of a tall, handsome forest of straight Ponderosa pines on the outskirts of the Deschutes National Forest. These cabins are spacious with wideplanked wood floors, king beds, fireplaces, Vintage-style artwork from artist Paul Lanquist, and Mission-style furniture custom made by Pennsylvania and Ohio Amish. “They brought the furniture in by the truckload and then filled the trucks with apples from Hood River before returning home,” says Greg Willitts, FivePine Lodge facilities manager.

In one of its romance suites, a large soaking tub is built into the corner of the living room, adjacent to the fireplace. My wife dials in the hot water and out it spouts from between cultured stones that form a partial embankment around the tub. Nobody puts baby in the corner … unless, of course, it’s to relax in a soaking tub in the middle of the forest.

The nearby Three Creeks Brewery serves comfort food and very good beer. The regimen includes a light and busty Knotty Blonde, a spicy Hoodoo Voodoo IPA and a lovely chocolate malt masquerading as a porter. The Clancy Brothers’ love song (I’ll a porter if I may, it makes me feel content and happy) influenced my desire this evening to be content and happy—twice, before we loaf it back to our cabin.

Across the parking lot from Three Creeks Brewery is the Sisters Movie House, or perhaps more accurately, movie barn. Inside the modern red barn, first-run blockbuster movies play across four screens. A full cafe serves food, beer and wine.


Oregon Trip Planner Day Two: Doughnuts | Snowsports | Good Eats


Mornings in Sisters take on the pastoral images of rebirth—a low sun slanting through tall pines and casting patterns of sun and shadow across the soft floor of the forest. It’s easy to forget that the rest of the world exists and not bother with what’s going on outside. Whatever they’re doing, chances are they’re not getting baked goods at Sisters Bakery before heading up to ski. Once the Leithauser General Store, built in the mid-1920s, it is now the Sisters Bakery—a throwback to a time when made-fresh daily doughnuts reigned without apology or remorse.

I’m three back in the line and anxiously taking in the last apple fritter out of the corner of my eye. It’s a must-win situation for me. The worst thing you can do is over-value the fritter in the jewel case with a direct stare and risk tipping off others with your selection priority.

The first of the two in line, I have pegged as a Maple Bar Standard—in his 20s, trucker hat touting nonsense and jeans falling off him like loose skin. “Umm, two ahhh two maple bars, please.” Bakery profiling has its scholars. The second in line and the final obstacle to the last fritter, is more enigmatic. She’s wearing jeans and what could be a Patagonia, Columbia or REI jacket. She’s appears to be closer to my age (not so old that she’s a straightticket Sour Cream Old Fashioned gal) and could have been raised in the Golden Era of the Fritter.

“I’d like a total of four doughnuts.” Her words shatter what’s left of my tenuous bakery patience as I nearly bark, “What the Fritter!?” I’ve been in this situation before, though, and experience makes a difference. I focus my attention on the cream-filled doughnuts in the case. “Two Bismarks and two buttermilk bars.” I should have known! The hoop earrings are a dead giveaway I overlooked. I played a fundamentally sound game and won. Joyous fritter!

A little more than twenty miles up Highway 20 and the Santiam Pass, is Hoodoo Ski Area. Hoodoo will remind you of some of the smaller resorts from an earlier era of skiing. It has thirty-two runs over a vertical drop of 1,035 feet. At the bottom of it all is a new lodge with rentals, a restaurant and bar. Since most of the skiing happens on the face visible from the lodge, parents can keep track of their kids from the bar, if need be. For kids, there’s also one of the state’s most extensive tubing parks on the other side of the lodge.

Ski alternative: If you want to earn your own turns and bomb fresh powder from Broken Top or the Three Sisters peaks, book ahead of time at Three Sisters Backcountry. With two yurts and full kitchens that share a wood-fired sauna at the base of Tam McArthur Rim, this is a wilderness treat.

Another possibility is to stop in Camp Sherman, just a few miles up the pass for fly-fishing’s other productive season on the pristine Metolius River.

There are certain institutions in Sisters whose regular visitation defies debate. One of those is Jen’s Garden, a tiny cottage with enormously flavorful food. Co-owners T.R. and Jen McCrystal, along with chef Caryl Hosler, would be a culinary force anywhere. There’s a five-course prix fixe, a three-course prix fixe and an a la carte menu that offers dishes such as risotto with baby shiitakes, Rogue Creamery blue cheese and roasted hazelnuts for a first course, beef tenderloin in a brandy and green peppercorn sauce with pommes frites for a second, and chocolate orange pot au crême for dessert.

A small-plate alternative is The Porch, a combination of gourmet, comfort food and small portions. Fried mac and cheese with smoked gouda and sage, duck confit empanadas, and shrimp and grits are just a few bites to share on this creative menu.


Oregon Trip Planner Day Three: Caffeine | Shop | R & R


Skiing or snowboarding may have beaten up your body a bit. Fortunately there are a number of remedies and no two the same.

FivePine campus includes the intimate and luxurious Shibui Spa. Herein sits a 125-year-old Buddha, a beautiful Japanese soaking tub and a number of treatment rooms where healing begins.

Another proven remedy is the contrarian postulate that soreness loves exercise. The Sisters Trail network weaves its way behind the lodge. There you can trail run for miles through the forest and connect up to the Peterson Ridge Trail. If there’s no snow at that elevation, bring your mountain bike for a mild and beautiful ride.

Finally there’s doubling down on baked goods. Macbeth best said “blood will have blood.” In a town of 2,000, there are shockingly good options. Angeline’s Bakery and Sisters Coffee Company are two exceptional cafes. Angeline’s specializes in gluten free and vegan fare—the kinds of things that you could eat daily without guilt.

Take something from Angeline’s or a house-baked scone from Sisters Coffee Company on a walkabout as you shop for your parting Western souvenir. Leavitt’s Western Wear on Cascade Avenue has it all—authentic boots, hats, Pendleton blankets and belt buckles.

A little farther down Cascade, Antler Arts is another Sisters one-of-a-kind. This is where to find your thirty-point antler chandelier and other antler- or hide-related items. The galleries such as Clearwater Gallery and Canyon Creek Pottery are worth browsing. Who knows in which little gallery you’ll find the next Georgia O’Keefe or Bernard Leach.

On your way back home along one of the most scenic drives over the Santiam Pass, stop in Black Butte Ranch for a salmon quesadilla or a bowl of chowder at the lodge restaurant with views of the Cascades. Take it all in from the past three days and write a postcard to a friend about this place that moon rockets thankfully missed. End with, Burn this.


Explore Sisters

What to Do

Ski at Hoodoo

Backcountry ski at Three Sisters Backcountry

Spa at Shibui

Where to Eat

Jen’s Garden

The Porch

Three Creeks Brewery

Bronco Billy’s

Los Agaves

Sisters Bakery

Angeline’s Bakery

Sisters Coffee Company

Where to Stay

FivePine Lodge

Lake Creek Lodge

Best Western Ponderosa Lodge

All photos by Erin Berg.

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