How many times have you visited an area and seriously thought: I could live here. Ask any friend who has traveled through the big blue sky, sage-brush speckled landscape of Central Oregon and that’s often what you’ll hear. There’s a wildness to the beauty here that ripples from the magnificent old-growth ponderosa pines to the briskly cascading Deschutes River.
Over the past decade, an influx of creatives inspired by the evocative landscape—and the region’s down-to-earth vibe—have turned many of the surrounding towns into hubs for art and innovation. While everyone is familiar with Bend, a town that’s like your smart, sporty and really good-looking friend, there’s more personality-packed pockets throughout Central Oregon to explore with cool restaurants and retreats emerging to delight both locals and visitors.
Wherever you visit, you’ll find a sense of possibility in the desert air that’s exhilarating. No wonder so many people dream about living here. But the next best thing is a jam-packed getaway where you can explore to your heart’s content. We’ve got you covered from what to see, where to stay and all the things to savor in this sun-soaked and star-studded stretch of Oregon from Redmond to Sisters and all the beautiful spaces in between.
What To Do
An obvious mecca for outdoor play, Central Oregon is also home to a fantastic arts community. In Bend, the High Desert Museum highlights the natural world and cultural history of the region with multiple galleries and rotating exhibits. The family-friendly center also has extensive outdoor exhibits that include resident otters and birds of prey. You can dive deeper into the history of the landscape and people that shaped the region at the Deschutes Historical Museum.
In Sisters, catch sensational mountain views on horseback riding tours for all ages and skill levels. Carve out some time for a drive on the McKenzie Pass-Santiam Pass Loop, an eighty-two-mile byway offering some of the best scenes in the state. Along the route is Clear Lake, where the lake is so glassy and pristine, kayakers can see ancient trees petrified by the water’s cold temperature as they paddle. Afterwards, keep a lookout for the road signs alerting you to the Sahalie and Koosah Falls, it should not be missed. Head to Smith Rock State Park near Redmond, to see one of the state’s most renowned natural wonders. In addition to miles of hiking and biking trails that crisscross golden river canyons, this is a bucket list spot for rock climbers from around the world. You can dive deep into geology at the Redmond Caves Recreation Area and then enjoy a serene stroll along the banks of the Deschutes River at Cline Falls State Park.
In the heart of Bend’s downtown, you’ll find nearly a dozen art venues including Red Chair Gallery and Scalehouse Gallery for contemporary artwork and Mockingbird Gallery for paintings and bronze sculptures by regionally and nationally renowned artists. Don’t miss the Tin Pan Alley Art Collection as you meander through town and the popular First Friday Art Walks.
For destination shopping, the town of Sisters offers a perfect mix of Western style (think vintage Stetson) along with Pacific Northwest classics like Pendleton. Swing by standouts that include Crazy Like a Fox Vintage, Dixie’s and The Jewel, where you’ll find one-of-a-kind pieces made by local artist Jan Daggett. Looking to add to your art collection? Don’t miss the contemporary Native American art at Raven Makes Gallery. For a remarkable collection of Vietnamese and Japanese artists, along with one-of-a-kind pieces from local and regional artists at Toriizaka Art.
Plan for an afternoon at Bend’s Old Mill District, a vibrant collection of restaurants and boutiques surrounded by miles of walking and running trails. Check the calendar at Kara’s Kitchenware store for popular monthly cooking classes. Or for a more neighborhood vibe, head to Northwest Crossing, where you can shop one of the best wine collections around at West Coast Provisions and find your next great read at Roundabout Books just up the street.
The only question when adventuring in Central Oregon is where to start? There are so many sublime spaces—lakes, rivers, forests, and caves—to explore in this natural wonderland. If you need a guide, Wanderlust Tours offers half-day naturalist-led trips throughout the year with options that range from canoeing and kayaking to stargazing and forage-to-table dinners.
Come summer, the Deschutes River turns into an oasis for play. You can explore the beautiful waterway by kayaking, paddleboarding, tubing, rafting or even surfing. The river (and many nearby lakes) also attracts anglers from around the world to cast in the pristine waters. Check out Bend Fly Shop, Deep Canyon Outfitters and The Fisher’s Place for guides and supplies.
But one of the best ways to immerse your senses in this juniper and sagebrush-etched landscape is to simply hike. You’ll find an astounding 70 miles of urban hiking trails within Bend’s city limits and hundreds of trails that wend through the surrounding pine and juniper forests.
Another popular mode of transit in the region from spring through autumn is on two wheels. Whether you are drawn to coasting mountain trails or speeding down gravel, there’s no shortage of rides to pursue. Tap local experts with Cog Wild—in addition to skills instruction and guide-led rides, they provide seasonal shuttle service to popular trailheads in Bend and Oakridge.
Whatever adventure you choose, don’t miss the iconic Mt. Bachelor, a majestic 9,065-foot marvel with four seasons of recreation fun for all. The destination is the seventh largest ski resort in North America and has one of the longest ski and ride seasons in the country (from Thanksgiving to Memorial Day).
Come summer, the Bachelor Bike Park offers lift-access mountain biking on two lifts and over 13 miles of spectacular bike trails. Other summertime activities include an 18-hole PDGA disc golf course and a truly epic zip line that’s hailed the “Northwest’s steepest, fastest, and highest-elevation zip adventure.”
Where To Stay
In the heart of downtown Bend, the Oxford Hotel’s stately and spacious rooms come with a variety of irresistible amenities including a pillow menu, complimentary cruiser bikes and a loaner Victrola Turntable and vinyl albums. Bonus: You can bring Fido, as the lodging is pet friendly.
Located 20 minutes south of Bend, you’ll find Sunriver Resort, an enchanting 3,300-acre community surrounded by forests of yellow-barked ponderosa pine and endless trails to explore. What sets this retreat apart from others? Sunriver’s picture-perfect 34 miles of paved and tree-lined pathways, a dream for cycling from your mountain home to the ten onsite restaurants, aquatic center, pickle ball courts, local art gallery, indie bookstore and more. For golfers, the resort hosts 63 holes spread across four scenic courses.
At the resort community of Black Butte Ranch, you can see seven of the Cascade’s majestic snowcapped mountain peaks in a hushed high desert refuge. Set near the charming town of Sisters, this cattle ranch turned luxury retreat spans 1,800 acres with a mix of elegant ponderosa pines, leafy aspen groves, and a pristine lake for fly-fishing. Guests can enjoy everything from mountain biking and hiking, to golf, swimming, canoeing, horseback riding, and more.
One of the wonders of Juniper Preserve, a 640-acre resort property set 20 minutes outside of Bend, is the swath of ancient juniper trees (some up to 1,000 years old) that surround the estate. At this recently rebranded retreat, guests can take advantage of wellness programming, restorative spa treatments, poolside barrel saunas, pickleball courts and world-class golf. A spectacular onsite lava cave is a wondrous home for singular activities that range from a cappella performances to wine dinners.
For stellar sunsets, Tetherow is the star. Located 20 minutes from downtown Bend, the sensational resort spans 700 acres and borders the Deschutes National Forest. An ideal spot for all seasons, the retreat is a short drive to the slopes of Mt. Bachelor and the Cascade Lakes. You can rent either modern vacation homes or stay in their 50-room boutique hotel. For amenities, there’s an award-winning 18-hole golf course, three restaurants and a state-of-the-art fitness facility with a heated pool and cabanas.
Near Redmond, the upscale Brasada Ranch entices with sweeping mountain vistas and hillside hikes through sagebrush. You can opt for one of their charming hotel suites or a luxurious cabin. Resort amenities include an onsite spa, horseback riding, pools, and a golf course. Take advantage of the remote location to soak up starlit skies in the evening.
Where To Indulge
In recent years, Bend has turned into a stellar culinary destination. For decades, the mountain town has been a leader in the craft beer movement (they’re at 26 and counting). But with a spate of new restaurant openings—some that entice Portlanders to road trip just for dinner—there’s a newfound electric energy to the food scene.
Make reservations at these newcomers for an unforgettable night out. First, the luminous Dear Irene, where chef Jonny Becklund turns out starters like roasted heirloom carrots and grilled cheese with black truffle honey. The jewel-toned wallpaper and lavish chandeliers give big city vibes and it’s a fantastic addition to downtown.
Head to the refreshed Bar Rio for festive tapas and cocktails from a citrus-kissed shrimp and mango ceviche to spicy chicken shawarma tacos. The more the merrier—and the more delicious plates you can order. So, bring friends to make this a tapas party. Another dinner party hotspot is Rancher Butcher Chef (RBC), this butcher shop-restaurant serves up sharable meat dishes (sourced from local ranches) and a signature poutine. But the standout salads and a sublime “quinoa under a fur coat” always wow the table too. Their recently opened downtown location focuses on creative tapas and cocktails.
Old-guard spots in town to check out include Ariana, a charming farm-to-table restaurant set in a craftsman bungalow run by a husband-and-wife team. For wine lovers, 900 Wall is your spot with more than 250 wines by the bottle and the largest selection of wines offered by the glass in Central Oregon (topping in at 65). For oenophiles, there’s a host of wine bars in town but you can also day trip to the region’s leading wineries and vineyards including Faith Hope & Charity Vineyards and Maragas Winery.
At the popular Zydeco Kitchen, you’ll find dishes with a southern bent like a spicy jambalaya topped with shrimp and crawfish and gumbo stuffed quail. On the lighter side, there’s 5 Fusion and Sushi Bar, the go-to spot for modern Japanese dishes like Albacore sashimi drizzled with yuzu truffle vinaigrette and miso cod butter lettuce cups.
In Sisters, the Cottonwood Café serves an upscale breakfast, complete with brunch cocktails and a cute cottage backyard. The Rancho Viejo is the oldest Mexican restaurant in town and turns out tasty bites like chipotle taquitos and an avocado tostada salad. If Thai food is what you’re after, June’s Asian Kitchen offers great service and comforting cuisine. While in Redmond, Brickhouse is a must-visit for hearty classics like Filet Oscar and chicken piccata.
Where To Imbibe
An evening in Bend beckons—from brewpubs with perfectly piney IPAs and festive fire pits to stylish restaurant bars serving up creative cocktails, there are so many places and reasons to toast while spending a weekend in this high-desert city.
Getting There
Part of the magic of traveling to Central Oregon is the scenic drive, where you can see cityscapes transition to grand high desert vistas. You will know you are getting close by the crisp pine scents floating through the air.
If you are short on time, there are direct flights to the Redmond Airport from both Portland and Seattle. The cities of Sisters, Redmond, and Bend are a short drive away for all the adventures and shopping you desire. There are daily train and bus services, plus highways coming from all points north, south, east and west.