The Insider's Weekend Guide to Bend

Here's where to eat, shop, hike, float, and golf in the happiest city in the Oregon high desert.

By Ramona DeNies April 24, 2018 Published in the May 2018 issue of Portland Monthly

The city that centers Oregon’s high desert has a bit of a reputation: as a ski bum’s beervana, a putter’s paradise, a sandbox for the fit (and the retired). Bend, Oregon, is a lot of fun—but not just because it’s surrounded by world-class ski routes, trails, and manicured greens. Packed tight within its urban core, find a city thick with breweries and boutiques, white-water thrills and winsome vistas. In Bend, even the most buttoned-up visitors let their hair down—the better to soak up that glorious sun, splash in the Deschutes, and make straight for pints by the fire pit. (The next day, hit repeat.) Here are a few of Bend’s newest highlights, along with the classics that keep us coming back.

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Stand-up paddleboarding on the Deschutes

For River Rats

What makes Bend so cool in the blazing summertime? That sliver of river cutting right through town. Fed by Mount Bachelor snowmelt, the whole length of the wild and scenic Deschutes River is wonderfully runnable. But just north of the city’s historic Old Mill District, the two-year-old Bend Whitewater Park offers something nature cannot: a cascade of four permanent waves, controlled by pneumatic underwater bladders, perfect for year-round river surfing. Spectators can gawk at the popular three-channel waterpark—one run is for whitewater adventurers, one for leisure paddlers, and one reserved for wildlife habitat—from a pedestrian footbridge paralleling Colorado Avenue. There’s plenty to see; last year the park drew an estimated quarter-million waterbabies. Longer river runs are also close at hand: Tumalo Creek Kayak & Canoe touts a self-guided “Townie Float” by inner tube. At Riverbend Park, Sun Country rents stand-up paddleboards for you and a furry best friend (optional). Brought your own flotation device? Between mid-June and Labor Day, Cascade East Transit’s Ride the River shuttle service cycles every half-hour between Riverbend and Drake parks; purchase a $3 day-pass wristband and you’re golden.

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Dramatic Cascadian vistas from the peak of Pilot Butte

For Trekkers

If you’re a runner or mountain biker, you already know: Bend is one of the world’s best destinations for trail training. Could have something to do with the water-hugging 19-mile Deschutes River Trail—which loops south from the Old Mill District into the Haul Road Trail, which segues into the Tetherow Trail, which connects to yet more trails leading to footbridge-dotted Shevlin Park and Phil’s Trail (the latter actually a monster mountain biking complex). Or, get down with one simple, spectacular view—that’s what you’ll find after a steep, one-mile climb to the summit of smack-in-town Pilot Butte. From here, a slew of cinder cones dominate the west, hinting at the grandeur of once-massive Newberry Volcano; to the east, survey the secluded Blue and Ochoco Mountains. But the city parks system’s shiniest gem might be Riley Ranch Nature Preserve. Open since December 2017, the tranquil wildlife refuge contains more than six miles of paved and soft-surface trail through juniper forests and river canyon. Seven miles south of city center, the permanent collections at the High Desert Museum showcase life in the area, from diverse human history to endangered native fauna.

For Souvenir Hunters

In Bend, if your business is the outdoors, chances are it’s booming. In the Old Mill District, look for a growing inventory of specialized local products—Ruffwear’s camp-friendly canine gear, Hydroflask’s insulated tumblers and growlers, “battle-tested” kayak and canoe paddles from Kialoa—on shelves up and down shopping-intensive SW Powerhouse Drive. (While on that strip, check in at the Ticket Mill for last-minute seats at the Les Schwab Amphitheater just across the river. Ray LaMontagne plays here in May; later in summer, there’s Jackson Browne, the Decemberists, and Portugal. The Man.) That ethos even inspires Bend’s canna-preneurs; Strong Silicone makes “bombproof” bongs, while high-desert dispensary Oregrown has a line of stylish merch—caps, hoodies, and raglans—sported by its sponsored team of bikers and ’boarders. More mind-altering finds line the Bend Inhale Trail (local makers Magic Number and Ablis are CBD soda pioneers). For picnic and kitchen supplies, try the Central Oregon Locavore market, stocked with artisan home goods, roasty beans from the likes of Lone Pine, and a dizzying selection of off-the-chain produce, locally ranched meats, and heirloom seeds.

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Clockwise from top: sleek steak house Bos Taurus in the heart of downtown Bend; cauliflower heart at Ariana; the sprawling lawn at Crux Fermentation Project

For Chowhounds

All that activity makes space in a traveler’s tummy; if you’re in Bend, you fill it (just a bit) with beer. Yes, Portland’s hop-loving cousin to the east competes with our brewing scene and sometimes wins; witness the city’s 15 medals at the 2018 Best of Craft Beer Awards. Start big—at the boisterous Sunriver or 10 Barrel brewpubs on NW Galveston Avenue—or go nano, at Ale Apothecary’s year-old tasting room seven blocks south, where the ales are wild fermented, barrel-aged, and available only Thursday through Saturday. For hearty grub with your suds, head to Crux Fermentation Project, where the lawn is dotted with cornhole sets and fire pits, and flanked by food carts. (Don’t leave without scarfing at least one cheesy, chile-packed Oaxacan taco from El Sancho.) Right down the street, ultra-chic coffee shop/bar Spoken Moto doubles as a chopper repair shop; pair your latte with a cardamom-flecked Ocean Roll from nearby Sparrow Bakery and pop next door to the Workhouse for Last Saturday live music, food carts, and art.

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The Hopservatory at Worthy Brewing

Dinner in Bend is usually a dressed-down affair, but the culinary rigor at posh steak house Bos Taurus bucks that trend, with an obsessively curated menu that spans rare Hokkaido Wagyu, “chef's whim” soups, and an artful wedge salad. A block from 10 Barrel, Ariana serves upscale Northwest classics—radicchio with Oregon pear, Dungeness crab risotto—from a light-filled Craftsman bungalow. For a nightcap by starlight, visit the Hopservatory at Worthy Brewing; this three-story tower adjacent to the brewery houses an honest-to-god mini Hubble telescope. Open-house viewings are nightly on weekends, and you’ll need to leave your beer outside; the better to spot space marvels under the supervisory eye of observatory manager Grant Tandy.  (We're talking everything from Saturn’s moons out to the Andromeda Galaxy, some 2.5 million light years away.)

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The golf course at Tetherow

For Golfers

Sunshine, dry heat, stunning mountain views: there’s a reason Bend is one of the world’s top golf destinations. Ritzy, green-ringed resorts surround the city. And yes, you could spend a day at Sunriver, Pronghorn, or Brasada Ranch, each within 20 miles of Bend. But be forewarned; by happy hour, you'll probably be sorely tempted to invest in a timeshare. For Bendites, prime putting is also closer at hand. Three miles east of downtown at Scottish heathland-inspired Tetherow, zip around an 18-hole course on a two-speed golfboard. At the Old Back Nine, a nine-hole public golf course five miles south, the mature pine forest is shady and the rates are reasonable. And on the northwest edge of town, River’s Edge offers 18 challenging holes on a Deschutes-hugging, lava-studded course originally designed by Robert Muir Graves.

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The Wall Street Suites’ communal fire pit, tucked just outside a clutch of guest rooms

Where to Stay

Housing in Bend is notoriously tight; a shortage partly fueled by recent waves of Silicon Valley transplants. We empathize, Bendites, but your pain has a silver lining: more private vacation rentals for us! Add to the inventory the latest location of Seattle-based Loge Co’s “intelligently designed hostels.” Loge Entrada (rooms from $120), a reimagined motor inn located near Tetherow, aims to lure sporty millennials with saunas, bike and ski tune-up facilities, and on-site bouldering. At the Historic Lucas House Bunk and Brew (bunks from $35, rooms from $69) just blocks from Drake Park, the laid-back staff offers a more traditional hostel experience, with funky furniture, an honor bar (beer, breakfast), an opt-in social calendar, and informal beer crawls. Half a mile north, the modest motel façade of the Wall Street Suites (rooms from $185) masks the upscale comfort of its horseshoe of suites: most boasting recessed lighting, skylights, and sleek, fully equipped kitchens. Meanwhile, downtown’s Oxford Hotel (rooms from $299) delivers patrician luxury—chocolates on pillows, complimentary glasses of wine, and a subterranean jazz bar.

Top image: A bird’s-eye view of two year-old Bend Whitewater Park (that’s Pilot Butte to the left).

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