Bend, Oregon


Hailed as one of the best towns in the country by residents and visitors—oh yeah, and reputable sources such as Outside Magazine—Bend is an outdoor enthusiast hub with a bit of urban cool.


The Tower Theater in Downtown Bend, Oregon
The Tower Theater in Downtown Bend, Oregon

“Farewell Bend” was a village composed of a few makeshift buildings on the banks of the Deschutes River—the last hospitable spot pioneers saw on their epic wagon train journey west over the Cascade Range. Leaving the “Farewell” behind, Bend has remained hospitable as a hub of outdoor sports competitions and recreation.

Outside Magazine called Bend the “Best Multisport Town” in 2017. Races range from triathlons and multisport to skiing, running and mountain biking. For the not so hardcore athletes, there’s a lazy float down the Deschutes River through Bend’s Old Mill District. Hikers will love the sixty-three miles of urban trails, including the Deschutes River Trail. Playtime is plentiful, with eighty-two parks and open spaces in town. Pooches will appreciate the off-leash areas in many local parks. To complement Bend’s recreational options, a vibrant cultural arena is alive with art galleries, art walks, a full schedule of outdoor concerts and a theater scene.

Makers gravitate to the High Desert, so locally made souvenirs are easy to come by. Making libations (and drinking them) is another popular pastime. Local wine, cider, distilled spirits, and beer are all covered. If you are feeling formal, try one of the white-linen restaurants or keep it casual with great eats from a food cart.

DESCHUTES RIVER TRAIL Adjacent to Tumalo State Park in northwest Bend along the east side of the Deschutes River, Riley Ranch Nature Reserve is a 184-acre former ranch that is opening to the public in 2018. The property offers connectivity with the Deschutes River Trail from the state park south to Archie Briggs Canyon on Awbrey Butte. The land features open meadows, juniper and pine forests, unique lava flows, cliffs and the river’s rocky canyon.

WINTER IN BEND With Mt. Bachelor’s extensive terrain and Bend’s thriving mountain destination scene, winter snowbirds flock here. From stormy powder days to the more frequent bluebird days (those are known for powder, too), downhill and cross-country options abound.

Head up Cascades Lakes Highway from your lodging at Tetherow Resort or WorldMark at Seventh Mountain to access snow adventures or head down to town to check out the social scene in one of Oregon’s fastest-growing cities. Either way, you’re guaranteed to find fun in under thirty minutes from the town that called one of the “20 Best Mountain Towns in America” in 2017.

Sample Fall Itinerary:

If there’s a shoulder season in Bend, it might be the fall. To many, fall means football and beer. To others, it’s warm coffee and long walks in the changing leaves. Bend has all of that and more.

Get your day started right with a coffee at the Instagrammable Megaphone Coffee Co. (which shares a space with the Boss Rambler Beer Club if you want to swing by later in the day) or The Victorian Cafe — now that it’s sweater season, you can get away with the Vic’s notorious eggs benedict and its Proud Mary. Work up a sweat with a walk along the Deschutes River Trail, which runs through town and will offer plenty of opportunities to see the changing seasons and a bonus — surfers in the river on a manmade wave in the Bend Whitewater Park.

On Wednesdays through October 9, finish your walk at Bend Farmers Market downtown and grab all the fixings for a fresh meal at home.

For a bit more adventure, fall is the best time of year to mountain bike on Bend’s hundreds of trails or at Mt. Bachelor, the winter ski resort that increasingly offers off-season options like steep mountain trails for riders of all levels.

Whether you’re a beginner or a pro rock hopper, you can’t go wrong — rent a bike from Pine Mountain Sports or Hutch’s, then check Central Oregon Trail Alliance for condition reports on the local trails. Or swing up the Cascade Lakes Highway, which is a place for quiet solitude in the fall, with dozens of lakes suitable for standup paddle-boarding or just a hike with excellent views.

When you’ve worked up an appetite, head back to Bend for some grub. Spork will transport you to far-flung destinations with its spicy fried chicken and first-rate curries, or get a little bit of everything at the Box Factory, which is Bend’s coolest new hangout — and literally a former box and crate factory. Among the hip businesses holding down the site are Riff Cold Brewed Coffee, Bledsoe Family Winery’s tasting room, and Fix & Repeat, a great spot to grab a healthy meal. Don’t miss an afternoon snack from the Foxtail Bakeshop.

Bend is known for its beer for good reason, and autumn is the perfect time to try some new varieties. Fresh hop season, which generally starts shortly after Labor Day and gets into full swing in October, means the city’s dozens of local breweries will offer pints of limited release fresh-hop beers you can only get in the pub — try Crux Fermentation Project, which recently underwent a remodel and has a happy hour around each day’s sunset, or Boneyard Beer’s relatively new brewpub as starting points, then see how many you can visit on the Bend Ale Trail. The city also hosts an Oktoberfest each fall, complete with wiener dog races.

After you’ve tasted Bend’s finest brews, head downtown for an evening stroll through the many locally-owned shops and a show at the Tower Theatre.

If you want upscale dining, try downtown favorites such as Barrio or Zydeco Kitchen + Cocktails — get the barbecued shrimp and grit cake for an appetizer. If a low-key meal is what you seek, try one of Bend’s food carts, at The Lot or On Tap.

When you’re finally ready to call it a night, rest your head at The Oxford Hotel, a downtown boutique with exquisite extras, or try Wall Street Suites, a quirky option with tons of character.