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Why Bend, Oregon, Is the Perfect Weekend Getaway From Portland

By Sunshine Flint

11.27.19

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On Tap is among Bend’s several food truck collectives, where guests can eat, drink, and enjoy the outdoors.

Photo by Brennan Pebbles/Visit Bend

On Tap is among Bend’s several food truck collectives, where guests can eat, drink, and enjoy the outdoors.

With a new luxury hotel, a promising restaurant scene, and loads of outdoor adventure, this jewel of the high desert makes for the ideal escape from the City of Roses.

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On the eastern side of the Cascade Mountains, Bend is known for its outdoorsy vibe, winter and summer adventure sports, craft breweries, and touch of pioneer spirit (an offshoot of the Oregon Trail once went through the town). Just over three hours—or a 40-minute flight—from Portland, it makes for the perfect weekend getaway from the big city.

Sunshine, incredible views, and good cheer are in abundant supply in this former lumber town. Surrounded by juniper forest, ponderosa pines, and cattle ranches, Bend gets nearly 300 sunny days a year—the most in the state—which makes the pine-scented air feel even fresher and the peaks of Mount Bachelor and the Three Sisters sparkle brighter. Almost every weekend brings a festival to the walkable streets of downtown, and even chilly nights don’t deter locals from gathering to relax after a day’s adventure in the mountains, often around blazing firepits, or to sample the region’s numerous craft brews. Join them—and make the most of your side trip—with help from our weekend guide to Bend. 

Where to stay in Bend

The new Huntington Lodge is Bend’s first luxury boutique hotel.

One of Bend’s newest accommodations is the Huntington Lodge at Pronghorn Resort, set on one square mile within a Bureau of Land Management–protected area right outside of town. Surrounded by acres of western juniper forest and sagebrush, the hotel boasts a stylish lobby living room, done in muted tones that mirror the landscape and shelves filled with objets, books, and original works by local contemporary artists. There’s also a solid bar, which makes good use of juniper and other regional ingredients. The 104 rooms offer panoramic views of the white-capped Cascades beyond the large pool and verdant golf course. The resort grounds are also home to two subterranean lava tubes that guests can explore with a guide. 

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About 45 minutes from Bend, near the town of Sisters, the Suttle Lodge offers rustic-chic accommodations on the shore of Suttle Lake. The log cabin–style lodge houses 11 rooms with fireplaces and beds made up with soft wool blankets, plus a mix of one-room cabins (no bathrooms) and larger lakeside cabins (with full amenities). Guests can rent kayaks and canoes to take out on the 3.5-mile long lake, walk the looping trail around the water, or simply relax in an Adirondack chair with a craft cocktail from Skip lounge while watching the sun set behind the peaks.

Where to eat in Bend

When in Bend, you can’t miss the Ocean Roll pastry (cardamom, vanilla, and sugar rolled up in traditional croissant dough) at the Sparrow Bakery or the Salty Queen kouign-amann (caramelized croissant dough topped with smoked salt) at Foxtail Bakeshop, one of the 30 local businesses in the Box Factory, a dining and shopping complex in a former lumber mill on the banks of the Deschutes River. For other cheap eats, check out Bend’s well-established food truck scene, which includes a number of collectives such as the Lot, On Tap, and the Podski, where food carts like Toasty (grilled sandwiches), Tin Pig (Southern fare), and Tacos (tacos!) rotate throughout the week. 

Head to Cascada for the six-course tasting menu paired with local wines.

For brunch-seekers, Jackson’s Corner on Bend’s west side serves organic fare sourced from Oregon farms and local foragers. When it’s time for dinner, head to the Old Mill District, where chef Eric Rud, who left his San Francisco restaurant for Bend’s Boxwood Kitchen, makes all of his pastas, spaetzle, gnocchi, and rolls in house. Another solid choice is Cascada at the Pronghorn Resort. Here, chef Kevin Linde brings his deep experience on the Oregon Coast to six-course tasting menus paired with excellent pinot gris, chardonnay, and cabernet sauvignon from Oregon’s Willamette Valley and Washington’s Columbia County.

Bend has the most craft and microbreweries per capita in the state of Oregon, and the Bend Ale Trail is a great way to visit most of them. If you’d rather stay put, go to the oldest of the bunch, Deschutes Brewery, which boasts a restaurant and tasting room in the heart of downtown. For cocktails, Bend’s best speakeasy is the Broom Closet, tucked under the eaves of the McMenamins Old St. Francis School Hotel, where part of the fun is finding the Alice in Wonderland–style secret doors and hidden rooms off the crooked hallways.

What to do in Bend

Nobody lives in—or visits—Bend to stay indoors. It’s a given that every car you pass on the road has a bike, kayak, or skis attached to the roof, with the drivers on their way to a mountain trail, the Deschutes River, or one of the Cascade Lakes in the Deschutes National Forest, just west of town. The surrounding region was shaped by ancient volcanoes and lava flows and the hour-long hike to the top of 500-foot Pilot Butte, an extinct cinder cone near the center of town, is the best way to get the lay of the land. To the west are the snow-capped peaks of the Cascade Range, from Three Fingered Jack to Mount Bachelor to Mount Hood, and to the northeast and east are the juniper-covered, terra-cotta-colored high desert and Blue Mountains beyond.

Mount Bachelor boasts one of the longest ski seasons on the West Coast.

A 10-minute drive from town, Mount Bachelor has 4,300 acres of lift-accessible trails, plus new terrain parks, chairlifts, and magic carpets set to open for the 2019/2020 winter ski season, which is typically one of the longest on the West Coast with operations going through May. Visitors here will also find more than 34 miles of groomed trails for cross-country skiing and skating. 

Head west from Mount Bachelor on the Cascade Lakes Scenic Byway to experience miles of alpine scenery and more than a dozen lakes for fly fishing, kayaking, and paddleboarding. For something magical, visit at night and join Wanderlust Tours for a starlight canoe tour on Hosmer Lake, when you can see the Milky Way reflected in the black, mirror-like water. 

About 30 minutes north of Bend, the Crooked River lazily carves its way through the eroded volcanic towers of Smith Rock State Park, which offers some of the best rock climbing in the world, plus a variety of trails for hikers of all abilities.

The Munch & Music free concert series offers live music, delicious food, and local vendors.

Bend also wows with cultural activities and entertainment throughout the year. The historic Tower Theatre is the town’s top performing arts center, hosting Broadway and dance shows, live music, and lectures. During the summer months, the outdoor Les Schwab Amphitheater also features acts as varied as Robert Plant and the Roots. Annual events like the Bend Fall Festival, BendFilm Festival, and Munch & Music bring concerts, food trucks, vendors, and a street-party atmosphere, while Bend’s art galleries, public art spaces, boutiques, and shops stay open late for the monthly First Friday Art Walk, which also serves up live music, food carts, and artists’ stalls.

>>Next: Plan Your Trip With AFAR’s Travel Guide to Portland

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