When legendary mountain men, trappers, and explorers scrambled over Bend’s forests, peaks, and rivers in the early 1800s, there were moments, amid the plying of beaver pelts, the mapping, surveying, and general Manifest Destiny–type tromping, when they were simply knocked out by the snow-dusted volcanic peaks, endless stretches of ponderosa pine, and the sagebrush-scented serenity of the high desert. After camping along Tumalo Creek in what is now Bend’s beloved Shevlin Park in December 1843, famed US expedition leader John C. Frémont journaled, “The great beauty of the country in summer constantly suggested itself to our imagination; and even now we found it beautiful, as we rode along these meadows...surrounded by noble forests.”

Following the routes where Warm Springs/Tenino, Wasco, and Paiute tribes hunted, gathered, and traded for millennia, they scouted the timber that would attract loggers and lumber barons, transforming the area a century later. But by the early 1980s, Bend's timber era had run its course. The forests that built the town were logged out, environmental rules tightened, and national markets shifted. As the mills were shutting down, a new wave of pioneers was exploring all the ways to play on the sun-drenched east side of the Cascades, shaping Bend's future as a nature lover’s destination.

Locals (now legends) with modified old gear and boundless curiosity pioneered the ways those sports are practiced in the region: Bob Mathews and Bob Woodward were carving out cross-country ski trails; Gary Bonacker, Tim Boyle, and Don Ipock were bombing down Bachelor on cruisers in the earliest days of mountain biking; many of these same adventurers joined Dennis Oliphant tackling uncharted white water in army surplus rafts while Alan Watts was bolting routes on the volcanic walls of Smith Rock. That same spirit was driving recreation gear brands such as Metolius Climbing, as well as craft breweries and creative start-ups finding fertile ground here.

Decades later came the pandemic-inspired influx of new residents, as remote work untethered people from big cities, drawing the next wave—tech workers, entrepreneurs, and young families seeking space and a fresh, new lifestyle. The influence of more than 7,000 people having moved to Bend between 2020 and 2025 is palpable, accelerating the trends of chef-driven dining, craft cocktail and creative brewpubs, boutique hotels, spas, and music and theater venues, all with their own blend of mountain town personality and rustic-chic comfort.

Today, in the high desert east of the Cascades where ancient volcanic lava flows shaped the land, Bend simmers with a new kind of energy. The ponderosa pines that once fed sawmills now frame snowcapped mountain views from outdoor heated pools. Mt. Bachelor’s signature powder, dry and fluffy, forms the canvas for painting an idyllic way to unwind and play under bluebird skies. After a day filled with sun reflecting off the snow, your face tingling and lungs refreshed with alpine air, the local ritual is to wind down with a brew—handcrafted with water fed by Cascades snowmelt. And as the sky goes pink at dusk over the Three Sisters, your body tired and mind clear, you realize you've stopped checking your phone, settled into a new rhythm—and suddenly understand why some visitors never leave.

Where to Eat (and Drink)

Fuel for a day of adventure or linger over a latte at Sparrow Bakery, beloved for its ocean roll, a flaky, buttery cardamom swirl. Sandwiches on hand-rolled croissants bear poached eggs, bacon, avocado, arugula, and aioli—or for lunch, Waldorf salad and housemade soups. Pro tip for this popular café in the boutique-and-eatery-studded NorthWest Crossing neighborhood: Get it all faster at the walk-up window just to the right of the bakery’s front door. For a leisurely breakfast in Bend's historic, timber-era downtown, the Portuguese café Sintra specializes in Mediterranean and American riffs on classic eggs Benedict, omelets, soups, and sandwiches.

With cattle ranches stretching across the high desert surrounding Bend, tasting the terroir of the region’s rugged landscape means steak, with new steakhouses celebrating locally raised beef. Mosey to Rancher Butcher Chef in NorthWest Crossing where chef John Gorham, founder of now-closed Portland institutions like Toro Bravo and Tasty N Sons, fully embraces the pasture-to-plate experience epitomized by a 40-ounce, 30-day-dry-aged locally sourced cowboy rib eye for $232. For equally high-spirited conviviality and inventive cocktails and tapas, sidle into his lively and intimate Bar RBC downtown.

Get another take on Bend's beef scene from Food Network chef Brian Malarkey's Hawkeye & Huckleberry, also on Bend's west side. The modern cowboy cuisine, craft cocktails, and design aesthetic reflect his local ranching roots and LA polish. Carve into a range of cuts such as a thick 16-ounce rib eye ($75) or 32-ounce porterhouse ($125) and select a sauce: chile butter, chimichurri, tartar sauce, toasted béarnaise, horseradish cream, or house steak sauce.

But for those who balk at $100-plus steaks but still want a taste of Bend beef, Americana’s smashburgers win at a downtown location with a vintage drive-in feel. The OG, two 2-ounce patties, American cheese, caramelized onions, a secret sauce, lettuce, and tomato on a toasted brioche bun, is $8.

Bend's reputation as a craft beer destination has much to do with another downtown staple: Deschutes Brewery. The pub started up in 1988, on NW Bond Street near the corner of NW Greenwood Avenue, touching off the city’s tradition of microbrewing and still anchors Bend’s craft beer scene with its iconic beers and innovative small-batch releases. Without Deschutes, we wouldn’t have the Bend Ale Trail, a passport-style tour where participants collect stamps and earn prizes by visiting the bevy of breweries that have popped up downtown and beyond ever since. Among them is UPP Liquids in the buzzing Box Factory hub between downtown and the Old Mill District. UPP, which has gained national acclaim, brews IPAs bursting with resinous pine, a creamy undercurrent, and a note of grounding sandalwood. Microbrew aficionados may also want to zip to the north end of town to check out newcomer Terranaut Beer’s classic English and brown ales that helped it snare Small Brewery of the Year at the 2025 Oregon Beer Awards.

Where to Stay

Downtown Bend remains a stronghold for visitors, drawn to its historic charm and the Deschutes River Trail through Drake Park. For a well situated home base, consider the cozy-chic boutique rooms of The Oxford, which hosts live jazz shows in its ballroom.

Just a few blocks east, the burgeoning Bend Central District, a.k.a. the Arts District, hums with indie creativity and DIY energy. Funky Fauna crafts ales fermented with their proprietary wild yeast, captured from the air on a high desert winter's night. Nearby Dogwood at the Pine Shed is the spot for craft cocktails, food trucks, live DJs, and community events emblematic of the up-and-coming, trending neighborhood. Soak up vintage vibes at the Campfire Hotel, with 100 renovated, camp-inspired rooms, outdoor heated saltwater pool, hot tub, Diva Drag brunches, and a firepit lounge under twinkle lights.

For some, a visit to Bend is about getting to the mountain, which makes the smattering of resorts and inns along SW Century Drive a draw. At Tetherow, guests wake up to views of frost-covered, snow-dusted sagebrush. With Deschutes National Forest trails out the back door, it offers closer access to Bachelor yet is only about 15 minutes from downtown Bend. The resort has a 50-room lodge and vacation home rentals, an outdoor heated pool, pub, café, and fitness center, a self-contained fortress at the foot of the mountain.

Across from Tetherow, Loge is literally—and figuratively—a 180-degree alternative, the same location minus the luxe touch. At the former motor lodge reinvented for outdoor adventurers, you’re sure to find a mutton-chopped, waxed-mustachioed snowboarding tech worker wearing a beanie in the hot tub, or a kindred spirit fat-biking trails in snow. Meet cute while walking your rescue dog, grab a mushroom-adaptogen latte with oat milk at the lodge café, and head up the hill to shred.

Where to Play

Bend is the place where "being left high and dry" is considered a good thing. Wet weather whips off the Pacific and across the state, but when it hits the east side of the Cascades and 9,065-foot Mt. Bachelor, it's transformed into the area's signature dry, fluffy powder. As the seventh-largest ski resort in North America, it has runs for all skill levels, and some multiday adult passes come with free lift tickets for kids age 6 to 12. 

Nordic skiers will find plenty—nearly 35 miles—of groomed classic and skate skiing trails. More than six miles of designated snowshoe trails let just about anyone get their heart pumping along corridors of towering ponderosa pines with seemingly impossible amounts of bough-bending white drapery. When it's sunny, rosy-cheeked skiers bask in postcardio bliss with a beer on the porch of the log-cabin Nordic Center, or warm up inside by the cozy woodstove with hot chocolate from the café. (Daily Nordic passes are $30 for ages 19‑64 and $22 for ages 6–18 and 65+.)

For less of a workout and more of a rush, hop onto a sled dog ride. A team of eight barking athletes led by a professional musher with Oregon Trail of Dreams will zoom you through the forests near the base of Mt. Bachelor Ski Resort at up to 20 miles per hour. (Prices start at $225 for adults, $110 for children.) The snowy Deschutes National Forest around Bachelor is an especially good place for dark sky stargazing. Wanderlust Tours leads nighttime snowshoeing trips, complete with libations around the bonfire and guides who infuse the experience with an appreciation for nature.

But 2025 is an odd year: Bachelor hadn’t even opened for skiing and snowboarding as of mid-December, making winter trip planning a gamble. If it rains (or you're not a skier), the High Desert Museum is a must, and a fun way to gain an understanding of the region's natural world and cultural history. Award-winning, artful exhibits change frequently, and thoughtfully designed indoor and outdoor spaces offer daily programs and close-up views of native wildlife, such as playful river otters, porcupines, owls, falcons, eagles, hawks—even a vulture. Historical characters share tales of early Oregon homesteaders, too.

For a night on the town, start with a sunset stroll at Drake Park, then slip into Tin Pan Alley and the firepit tables surrounding San Simón; inside, amid candlelit brick walls and bohemian vibes, bartenders peddle “sophisticated debauchery,” shaking Wild Roots cucumber and grapefruit gin with génépy and Chinola passion fruit liqueur. Next door, the tiny Tin Pan Theater has just 28 red plush seats from which to catch an foreign film or a holiday screening of Die Hard.

Bend’s theater offerings have been steadily growing, while the drag scene is gaining real visibility. For professional theater in an intimate venue, venture beyond the downtown fringe to the Bend Central District. The Greenhouse Cabaret is tucked behind the trendy plant shop of the theater’s horticulturist-actor-founder, who stages top-notch performances from musicals to drag shows. Head to Volcanic Theater Pub, a black-box warehouse music space for everything from experimental synth-punk to rock, jam bands, and Americana.

In the morning, rejuvenate with a session at Gather Sauna House, a mobile, wood-fired sauna that parks beside a scenic spot on the Deschutes River right in town, so you can sweat, plunge in the bracing flow of snowmelt, and be renewed and ready for a day of adventure.

Beyond Bend

Bend is the clear cultural capital of Central Oregon, but the areas surrounding the city have their own draws.

For a remote backcountry adventure, book a snowcat to take you from nearby Mt. Bachelor to Elk Lake Resort for the day, or stay in one of their cabins—from rustic and vintage to ones that are more upscale, with a mountain-lodge feel. You can get there by cross-country skiing the 11-mile trail, mostly downhill; let the snowcat transport your gear and take you back to avoid the difficult, steep uphill.

As a bonus to any trip to Bend, consider following Highway 20 northwest of the city for a snowy detour through the Cascades. Begin with a stop in the Old West–themed Sisters, lined with shops, or head to Hoodoo Ski Area, a small, family-friendly, and low-priced mountain for easy, mellow runs and fluffy, abundant snow. Nearby, the Suttle Lodge in the Deschutes National Forest is where you can cross-country ski or snowshoe the flat 3.5-mile loop around Suttle Lake. Afterward, ramble back to the lodge for jazz and other live music by the fireplace hearth in the lodge’s restaurant.

Alternatively, if you’re traveling northeast into the more arid, desert-like region, try a few nights at luxury wellness resort Juniper Preserve, 15 miles from Bend. During construction of the eighth hole of its Tom Fazio Championship Golf Course, which opened in 2006, builders exposed a 60,000-year-old lava tube. Today, the resort hosts guided meditation and sound baths upon request in the cave-like formation that remains 50 degrees year-round. The lodge has a year-round, outdoor heated pool, barrel sauna, and hot tub with expansive views of twisted, old-growth junipers and the snowcapped Three Sisters mountains. Vacation rental homes are also available here, too. And in the morning, head to Smith Rock State Park. It’s world renowned for climbing, but the snow-dusted, terra cotta canyon walls rising above the winding Crooked River are a pinnacle of serene beauty. The 1.5-mile Canyon Trail has a steep slope at both trailheads but is accessible if you are vigilant about avoiding icy spots. Even a simple stop at the North Point Amphitheater at the end of the turnaround parking lot is worth it on a sunny, snowy day, before the long drive back to Portland.