Four Seasons in Sisters, Oregon

by Casey Hatfield-Chiotti

Photo Courtesy: Cody Rheault

I will always remember the first time I visited the town of Sisters at the base of Central Oregon’s Cascade Range. After growing up in Portland as the oldest of three girls, I’m sure my parents felt as though the former lumber town—named for the Three Sisters peaks which serve as the town’s stately backdrop—was a necessary stop on our big summer road trip. After only driving three hours, as Sisters sits 153 miles southeast of Portland and 22 miles northwest of Bend, we felt as though we’d entered another time and place. The Old West I had envisioned during school lessons about the Oregon Trail had suddenly sprung to life in Sisters.

An 1880s-style storefront theme was adopted by the City Council as part of its zoning ordinance in the early 1970s. It made for a town of clapboard buildings with covered porches along the main drag, and a population of residents who adopted a country-style way of living.

Many things in Sisters haven’t changed since those early days. Locally owned boutiques and sweet shops still line Cascade Avenue, and Sisters Bakery continues to have a steady line out the door. However, the notion of “country-style living” has evolved. Today, the town is filled with young families, food carts and a farmers market, where hip makers sell everything from vegetables and beautiful baskets to natural perfumes.

If you’ve never been, go. If you haven’t been in a while, find an excuse. There’s so much to see and do in Sisters every season of the year.

Spring: Rest and Rejuvenate

Photo: Fivepine Lodge

Sisters sits at the confluence of several stunning landscapes: the Willamette National Forest, the Deschutes National Forest, and the high desert to the east. While winter offers its own rewards, as the snow begins to thaw and the pine tree’s soft green needles unfurl, Sisters reveals itself as wellness destination.

The air is brisk and clean at the FivePine Lodge and Spa, where forests surround craftsman-style cabins and lodge suites. Guests can access the Sisters Athletic Club which has yoga, a hot tub and a lap pool, and the lodge’s Shibui Spa. The spa’s long treatment list offers an array of experiences, from a Himalayan Salt Stone massage to CBD-infused facials and body treatments.

When the unpaved road to the trailhead is is snow-free, hike to the top of Black Butte, an extinct stratovolcano 15 minutes from downtown Sisters. Climbing Black Butte is ideal in the spring before temperatures rise. The 1.9-mile hike to the summit is steep, but visitors are rewarded with a panorama of mountain peaks.

Hikers can reward themselves with root beers at the Camp Sherman Store on the spring-fed Metolius River or venture to The Suttle Lodge & Boathouse for whiskey sours and fried fish sandwiches. Reserve one of the lodge rooms or cabins and sit near a fireplace after an active spring day exploring the Cascades.

Summer: Best of the West

Photo: Nate Van Mol

In late spring and summer, Sisters is a western lovers’ fantasyland, with old-time events, plenty of camping options and one of Oregon’s best rodeos.

The Sisters Rodeo draws visitors from all over the state and beyond during the second weekend of June. Travelers can expect pageantry (a rodeo queen, flag flourishes) and all the rodeo highlights, such as extreme bull-riding, barrel racing and more. Plus, there’s a focus on honoring indigenous communities and cowboy traditions worldwide, along with the proper handling and caring for animals. The Sisters Rodeo is sanctioned by the Professional Rodeo Cowboys Association.

Big Ponderoo, an outdoor celebration of bluegrass and Americana music, sets up at the Three Creeks Brewing Production Facility stage for two lively, music-filled days at the end of June.

The free Sisters Outdoor Quilt Show each July showcases colorful works of stitched art. Quilt show organizers believe every quilt has a story and past participants have been inspired by everything from the works of Vincent Van Gogh to destinations around the world. This year’s theme is Dreamscapes, so expect imagination and whimsy.

Summer visitors can take advantage of the region’s fine weather and plentiful campgrounds. Three Creek Lake Campground, next to the Three Sisters Wilderness area, is an adventurer’s paradise. Old-growth forests surround 11 campsites near a lake, in a valley formed by glacial erosion and filled with a healthy population of rainbow and brook trout. Fish from shore or hike the Three Creek
Meadow Trail through a Douglas-fir forest.

Join the eclectic mix of vehicles parked at Sno Cap Drive In on Highway 20, a fixture in Sisters since the 1950s, for thick milkshakes, burgers, and scoops of homemade ice cream.

Fall: Festival Fun

Photo: Sisters Folk Festival, by Robb Kerr

In autumn, Sisters is a riot of warm hues and folk music fills the streets. The Sisters Folk Festival in late September is a one-of-a-kind event with seven stages throughout the downtown, from large tents to intimate venues in local businesses. The talent is impressive; a singer-songwriter playing in the historic church might just be the next big thing.

Sisters’ robust community of makers comes out to display handcrafted items and artwork at the Sisters Harvest Faire the second weekend in October. After an autumn hike or shopping excursion, visitors can mix with a local crowd at the top-notch food cart pod and tap house, The BarnBoone Dog Wood Fired Pizza serves bubbling pies topped with charred onions, Castelvetrano green olives and house-made Italian sausage which pair perfectly with the excellent array of frothy beers served in the barn-like setting.

The Cottage Inn at Sisters, a boutique hotel featuring six modern farmhouse-style accommodations, is within easy reach of Sister’s fall festivities.

Winter: A Mountain Wonderland

Photo: Pete Alport

Twenty miles west of Sisters, Hoodoo Ski Area offers wide-open terrain and deep powder on the backside. Night skiing at Hoodoo is a local tradition, and even visitors who don’t ski can have winter fun on the Autobahn Tube Hill. Nearby Santiam Sno-Park is a popular sledding area.

Many Hoodoo visitors choose to stay at Black Butte Ranch, a vast resort with a spa and more than 100 vacation rentals, from cozy to luxurious. When the meadows are blanketed with snow, winter is a magical time at the Ranch. Active guests can cross-country ski or snowshoe on groomed trails around Big Meadow Golf Course, and the holidays bring family carriage rides and a festive New Year’s Eve celebration.

At the end of November, the Holiday Tree Lighting in downtown Sisters is a community event with hot chocolate and cookies that will surely spark plans for a return visit.