: Gritchelle Fallesgon / Visit Central Oregon

Road Trip: Redmond

The heart of Central Oregon beats with great places to eat, sleep and play.
February 26, 2014 (Updated February 21, 2023)

Sitting at the crossroads of Central Oregon, Redmond has blossomed into a destination in its own right, with excellent cycling trails, great food and unique shopping, all tucked between two gorgeous national forests. The city of 33,000 people and counting seems to boast a sunny high-desert attitude year-round, making it a delight to visit anytime. Here’s how to make the most of it.

Interior of a hotel lobby.
(Courtesy of SCP Redmond)

Make Downtown Redmond Your Base Camp

Back in the day — which is to say, relatively recently — if Redmonders wanted a night out, they often came to Bend. No more. Redmond’s list of things to eat and do has exploded in recent years, so much so that now even Bendites are starting to make the 20-minute drive north to sample the goods. 

Base yourself at the SCP Redmond Hotel, a small wellness-focused chain that aims to leverage your visit into real opportunities to help others, guests included. The 49 rooms and suites sit in the heart of downtown in one of the city’s most iconic brick buildings: the old Redmond Hotel. Each room comes with yoga mats and essential oils but not an alarm clock. There’s a sun terrace and a rooftop bar and lounge with craft cocktails and small plates like mezze platters and a watermelon-mint salad. Try the vegetarian Persian stew at the on-site Terra Kitchen restaurant.

Every time you stay, the hotel uses some of the proceeds to help kids in need and to help reforestation efforts. What’s more, the staff is so confident that you’ll love your stay that you’re welcome to pay what you think your stay was worth based on the quality of the experience. 

In winter, bring your ice skates (or rent them onsite) and take the family to the city’s outdoor rink near the Visitor Center. The rink is generally open from the end of November through mid-February and tickets for the whole family cost $20 for up to six people.

Food shot of barbecue chicken pizza.
(Courtesy of Cascade Lakes Brewing Company)

World Cuisine and Northwest Brews

Within a few short blocks, you can travel a world of culinary flavor. Oishi Japanese Restaurant has fantastic sushi, sashimi, tempura and bento boxes. At Diego’s Spirited Kitchen, you’ll find a diverse menu of Mexican food and margaritas — plus a great wine list. Try the giant platters of carne asada or mar y tierra (surf and turf). Just want a steak? Brickhouse downtown has you covered. 

For good, old-fashioned Northwest pub grub and brews, don’t miss Cascade Lakes Brewing Co.’s Seventh Street Brewhouse or Wild Ride Brew offers creative beers like a peanut butter stout. The property also features food carts like Wild Catch, offering up English-style fish and chips, and Shred Town, which makes awesome Cuban sandwiches. General Duffy’s Waterhole & Annex, another food-cart pod a few blocks south of Wild Ride, has 30 beers on tap and five food carts. Don’t miss the crispy garlic chicken at Baitong on Wheels.

Awesome Antiques and Boutiques 

The heart of Redmond is a wonderful place to stroll and shop among a collection of boutiques and stores. Herringbone Books has a great selection of books and gifts for kids and adults. For board sports, Redmond Snow and Skate is a must. Antique lovers will find a treasure trove of options at Beyond the Ranch Antiques, Redmond Antique Mall and The Back Porch & Company.

Woman recreation climbing on overhanging Maple Avenue Bridge.
(Courtesy of Visit Redmond)

Rodeos, Rides and More Ways to Get Outside

In April you won’t want to miss the High Desert Stampede at the Deschutes County Fair & Expo Center, which brings together some of the best athletes and storied livestock in a show that celebrates great horsemanship and sheer bravery. It’s one of many rodeo events held during the season, including the Deschutes County Fair & Rodeo — which is over 100 years old — each August. 

Smith Rock State Park sits about a 20-minute drive north of town, where you’ll find spectacular hiking among the cool waters of the Crooked River and volcanic cliffs that bring rock climbers from around the world. Go in early spring, late fall or winter for fewer crowds and crisp breezes. Redmond is also a great jumping-off spot for the Sisters to Smith Rock Scenic Bikeway, a 36.5-mile ride from town to the park. 

For something more unusual, check out the Maple Avenue Bridge, a 70-foot-tall, 780-foot-long concrete bridge over Dry Canyon, where artificial climbing holds and bolts run up the overhanging spans for some wild climbing for experienced climbers. The Dry Canyon Trail runs for nearly 8 miles through town, making it a great place to hike, run or ride a bike. Pro tip: When fresh snow falls, bring your cross-country skis and head out before it all melts away.

Radlands, an ten-mile trail system on the east side of town, is a fast, fun mountain bike ride with awe-inspiring views of the Three Sisters volcanic peaks and the high desert. “It’s pretty flowy,” says Eric Healie, owner of Trinity Bikes. The trail can be hiked or cycled in four seasons. West of town, check out the Cascade View system, a 12-mile network of singletrack trails.

About The

Tim Neville
Tim Neville is a writer based in Bend where he writes about the outdoors, travel and the business of both. His work has been included in Best American Travel Writing, Best American Sports Writing and Best Food Writing, and earned various awards from the Society of American Travel Writers and the Society of Professional Journalists. Tim has reported from all seven continents and spends his free time skiing, running and spending time with his family.

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