How to Get There
You can fly nonstop from San Diego to Portland, then rent a car and drive about three hours to Bend. Alternatively, you can travel nonstop from LAX to Redmond Municipal Airport, about 30 minutes from Bend. Alaska Airlines is adding a direct flight from San Diego to Redmond in January 2020.
Check into Loge Bend (double rooms from $150), a former motel four miles from downtown that’s undergone a hip reboot. It feels like an outdoor-lover’s playground, with bike rentals, fire pits, grills, a pool and hot tub, and quick access to Mount Bachelor, known for its skiing, disc golf, and mountain biking. Accommodations range from bunk beds to a deluxe king with an in-room sauna, and many rooms come with a hammock. If you’re seeking something more central, the 59-room Oxford Hotel (from $250) is a luxe downtown option that runs on 100 percent renewable energy.
Stretch your legs and head to Pilot Butte State Scenic Viewpoint, a 480-foot-tall cinder cone, where you can take the one-mile paved route or the steeper, slightly longer dirt path to the peak. Up top you’ll see a panorama of the city that includes Mount Hood and the snowcapped Cascade Mountains. From there, make it in time for sunset at Crux Fermentation Project, a tasting room (casual enough that your hiking attire won’t bat eyelids) that offers a prime seat to watch the sun dip. They have over 20 brews on tap, kombucha by Bend brand Caboost, and eats like a grilled cheese on Kettle Chip–crusted bread and a soft pretzel with spicy beer cheese. Crux is part of the Bend Ale Trail, a network of 18 beer spots, many within walking distance of one another.
Head downtown to local roasters like Thump Coffee or Companion Coffeehouse before taking an a.m. stroll on the Deschutes River Trail, which runs through downtown. In the summer, the area draws stand-up paddleboarders and tubers, while fall makes for a crisp walk past ponderosa pines on a dirt path. A pleasant, U-shaped route starts at Riverbend Park and heads south before crossing a bridge to the opposite side of the river. Walk north until you hit Farewell Bend Park.
Grab an early lunch at Spork, which blends Latin American and Asian influences in its lineup of pozole, rice bowls, and green curry. Then, it wouldn’t be a visit to Bend without some outdoor adventure. Wanderlust Tours is armed with a tribe of knowledgeable guides who lead excursions like snowshoeing with a stop for beers late November through March and canoeing on Mount Bachelor–facing lakes in the summer.
After you’ve cleaned up, meander through downtown’s Drake Park, a 13-acre riverfront green space adjacent to brewpubs, cafés, and restaurants. Walk over to dinner at Joolz, led by Beirut transplant chef Ramsey Hamdan. He blends his father’s Lebanese heritage with his "rodeo queen" mother’s Oregonian upbringing for a menu of Middle Eastern plates like kibbe and fusion dishes like Moroccan "camel wings" (chicken). If you have room, grab a scoop of Oregon marionberry sorbetto at nearby Bontà Gelato.
Start your day with a cold brew at Riff Taproom, a colorful food and drink spot that specializes in smooth nitro pours. Then it’s 16 miles east (40 minutes by car) to Tumalo Falls (the last three miles of the road is gravel, so an SUV helps). There’s a five-minute uphill walk to a great vista and a variety of trails in the area for hikers and mountain bikers. The road to the falls closes seasonally and reopens in April or May, but it’s still plenty fun in winter months: snowshoers, park at the gate at Road 4603 and trek 2.5 miles each way to the waterfall; skiiers, start at Skyliners Sno-Park, head to the end of Skyliners Road, then cross the bridge to Road 4603 for a seven-mile excursion.
Locals love El Sancho, a taqueria serving carnitas, barbacoa, fried shrimp, and potato with rajas tacos among other options. Pair it with their fried plantains and a house agua fresca. If brunch fare is more your thing, head to The Sparrow Bakery’s new location in the Northwest Crossing neighborhood. They’re famous for their Ocean Rolls—a buttery croissant dough sprinkled with cardamom, vanilla, and sugar—but their Bacon Breakfast Sandwich (and Not-So-Bacon version) are dynamite, too. Walk it off with a stroll to nearby shops like West Coast Provisions, a shop of food products, stationery, and wine sourced from Oregon and surrounding states, and vintage clothing at Cosa Cura. There’s more indie shopping to explore downtown: beauty products at Wren and Wild, ceramics and jewelry at The Feather’s Edge Finery, and paperbacks at Pegasus Books of Bend.
Bend is a town where the dress code is typically athletic wear and every car has a bike or kayak rack. But you’ll want to dress up for this meal. Housed in a Craftsman bungalow, the reservations-necessary Ariana is a fine dining option that pulls from Pacific Northwest sources and incorporates catchy ingredients like stinging nettle. The five-course, $70 tasting menu is an epic way to end the trip—you’ve done enough hiking, snowshoeing, and waterfall-trekking to earn it.
The Best Reasons to Extend Your Trip
Smith Rock State Park