Whether hitting the trails or the town, Sisters has plenty to offer, including world-class singletrack, road bike routes, dining and entertainment.

Written by Cathy Carroll 

The trails that Native Americans made as they gathered huckleberries, fished and hunted were followed by fur trappers and explorers before becoming settlers’ wagon roads through forests surrounded by the Three Sisters peaks. When the first post office was to be established here in 1888, it was to be named for those mountains, but postal officials went with, simply, Sisters. In this spot where the McKenzie and Santiam roads meet, itinerant sheep men passed through for sustenance and supplies en route to grazing pastures in the Cascades. It later thrived as a timber town until 1963, when the last mill was shut down.

Today, the spirit of its history remains, with the old West-style down-town façades, and the same mountain vistas and towering pine trees that call for breathing deeply the forest-scented air. Spring is a great time to soak it in, before the peak season kicks off with annual traditions—the Sisters Rodeo in June, followed by the Sisters Outdoor Quilt Show in the second weekend of July. An entrenched community of artists and outdoor enthusiasts mingle with small-town friendliness to form the atmosphere. Don’t be surprised when you’re walking into a local brewery on a busy Friday night and the person behind you says, “Howdy—we can share a table if you like.”

The slower pace and open spaces inspire a range of artists, especially folk musicians and singer-songwriters. The Sisters Folk Festival, held every year on the first weekend of September, is the apex of this folksy spirit. Not to worry, live music is easy to find year-round at intimate venues such as Angeline’s Bakery and Café or at The Belfry, a performance space created in a 100-year-old church. Picturesque trails and quiet, country roads beckon, too. Trails begin just six blocks from the downtown streets lined with galleries, shops and restaurants. At just a fraction of the size of Bend, Sisters offers the pleasurable option of being car-free and carefree, inviting the calm that comes with exploring on foot, as did its earliest residents.

eat

Cottonwood Café Pacific Northwest and traditional breakfast fare served in a quaint, family-friendly cottage and backyard with a fire pit and heaters. Well-behaved pups are welcome on the patio, too.
Sisters Meat and Smokehouse Grass-fed, hormone- and antibiotic-free Oregon meats, cheeses, and a knowledgeable staff that can offer advice on how best to prepare their ingredients. Serving sandwiches, wine and beer.
Cascade Street Distillery Family-run, small-batch distillers of bourbon, gin and vodka.
Latigo Fine dining inspired by ingredients from the ranches and farms of the Pacific Northwest.

stay

FivePine Lodge & Spa The main lodge blends modern and rustic architecture, incorporating the design elements of historic forestry stations. A thirty-foot rock fireplace is at the center of the lounge with eight suites. Twenty-four modern, craftsman-style cabins wind through a sprawling pine forest. Shibui Spa taps Asian elements to create a serene atmosphere. Relaxation rooms have fireplaces, and a thermal soaking tub is adjacent to a private sun deck. The FivePine “campus” includes a conference center, Three Creeks Brewery, Sisters Movie House and Sisters Athletic Club.

Sisters Bunkhouse An intimate inn with four rooms, each with a queen bed and private bathroom, and innkeepers who strive to offer exceptional service.

arts

For live music, check out Angeline’s Bakery and Cafe or The Belfry. Looking to kick up some dust with a more raucous crowd? Try Hardtails, a “biker” bar that doesn’t require patches and hosts plenty of live rock and roll bands.

Galleries throughout Sisters stay open from 4 p.m. to 7 p.m. every Fourth Friday for the Sisters Arts Stroll. Each month, galleries feature artists, serve light refreshments and sometimes host live music.

play

Hoodoo Spring skiing typically lasts until mid-April at this uncrowded, affordable, family-friendly ski resort with three high-speed quad lifts, thirty-two runs, and 806 skiable and rideable acres.

Biking Once the snow melts, excellent singletrack for mountain biking abounds, along with premier road biking. Eurosports offers free maps and information about nearby trails and scenic road rides for all abilities. The Peterson Ridge trail system has more than twenty-five miles of singletrack that begins a few short blocks from downtown. The Sisters Stampede mountain bike race on May 28 is Oregon’s biggest mountain bike race with 500 participants tackling the Peterson Ridge trail system. It begins and ends at FivePine Lodge.

Other rides, flat to rolling, range from the fifteen-mile Indian Ford Loop to a fifty-mile jaunt around Camp Sherman. For an epic climb, the thirty-mile McKenzie Pass ride is a state jewel. Climb 2,000 feet through ponderosa pine forests, follow an 1860s wagon road and emerge above the tree line to reveal a staggering view of Mt. Washington and a 2,000-year-old lava flow. This ride runs along state Highway 242, which is on the National Register of Historic Places. The pass is closed during winter, but the state Department of Transportation briefly opens the pass only to cyclists for a short but glorious window after they plow the roads in spring. Check tripcheck.com or rideoregonride.com for updates.