In central Oregon, the Old West still exists amid the rising ritz. See where to stay and what to do

Sisters comes by its rep as a ranch hub honestly. But any dirt in the air over this central Oregon town, on the fringe of the high desert, is more likely to be kicked up by mountain bikes along red cinder roads than by bucking broncos during its annual rodeos.

Despite Sisters’ 1800s-style architecture (strictly regulated by the town’s building code), don’t expect to see cowboys on horseback galloping through the streets. Not here, where art galleries now outnumber saloons and where newcomers ― the population has nearly doubled since 2000 ― arrive in SUVs, hungry for something more than bacon and beans.

What you’ll find these days is a town that’s as comfortably New West ― with an upscale spa offering a “Dance of the Desert” signature body treatment and a tiny destination restaurant serving dishes such as duck breast with a lavender-blueberry-anisette reduction ― as it is wistfully Old West.

It’s the ranch nostalgia, though, that has me hooked: tangible evidence of a less complicated life, closer to the land. Something about the window displays in Leavitt’s, a western-wear fixture on Cascade Avenue since 1977, always draws me in, stirring some preternatural rodeo-queen longing. Most of the clothing, I suspect, will never feel the chafe of the saddle; it’s STYLE IN THE SPIRIT OF THE WEST, as the sign in the window reads. The front showroom is filled with racks of cowboy and cowgirl finery ― the embroidered and fringed shirts, the tight boot-cut jeans. Up a flight of stairs is the hat room, stacked with Stetsons and the like; and below it the boot room, redolent of leather and the promise of a Texas two-step.

A similar longing pulls me to the Stitchin’ Post, just up the street. It’s one of the West’s great quilting shops, with bolts and bolts of fabrics, fun patterns ― and gorgeous finished quilts, which inspire me to continue the one I started years ago. Nearby is Bronco Billy’s, a local institution housed in a 1912 building and a reliable spot for grilled burgers and barbecue. 

Eventually I emerge from my time warp, and head south of the main drag, Cascade, to browse a burgeoning cluster of art galleries, antiques shops, cafes, and boutiques.

That’s where I find Jen’s Garden, with its linen tablecloths and ever-changing four-entrée dinner menu. A few blocks southeast is FivePine Lodge, just opened in May, and its Shibui Spa, with a high-desert-meets-Zen ambience.

Thankfully, ranches still encircle the town ― with elk, llamas, cattle, and horses. Hinterland Ranch is just 3 miles away, and visitors are welcome to stroll the grounds and get nose-to-nose with members of its 170-llama herd.

For a real taste of Old West living, I head to Long Hollow Ranch, 13 miles from town and about a century out of time. Tall poplars line the road leading to the yellow farmhouse, where I’m just in time for lunch on the broad veranda: sandwiches, homemade pickles, potato salad, sliced tomatoes, and berry pie.

Originally part of the huge Black Butte Land and Livestock Company, Long Hollow started taking paying guests just seven years ago, owner Dick Bloomfeldt tells me between bites. That’s apparently nothing in ranch years. Many folks come for a week or more ― especially the foreign tourists who make up more than a third of the clientele. In the off-season, the ranch welcomes weekenders too with trail rides through junipers and the promise of helping head wrangler Alicia Lettenmaier care for the horses. They have me, though, at the homemade pickles. 


  • Sisters is 20 miles northwest of Bend (about 150 miles southeast of Portland) on State 126/U.S. 20. 866/549-0252.





  • Leavitt’s 100 E. Cascade; 866/549-6451.
  • Stitchin’ Post 311 W. Cascade; 541/549-6061.



  • Bronco Billy’s Ranch Grill and Saloon Prime rib and burgers. INFO: $$; 190 E. Cascade Ave.; 541/549-7427.
  • Jen’s Garden Small but impressive seasonal menu. INFO: $$$; closed Mon through Sep 30, Mon-Tue from Oct-May, and entirely in Jan; 403 E. Hood Ave.; 541/549-2699.



  • Black Butte Ranch Rent a condo and enjoy golf, swimming, and trail rides (through mid-Sep). INFO: From $100; 866/901-2965.
  • FivePine Lodge New development with 24 cottages, 8 lodge rooms, and Shibui Spa (720 Buckaroo Trail; 541/549-6164); Pleiades restaurant is set to open in October. INFO: From $169 through Sep 15, from $139 Sep 15-May; 866/974-5900.
  • Long Hollow Ranch Ranch stay (including all meals and activities) from $185; lodging and breakfast only from $99; 877/923-1901.


Keep Reading: