Hiking up the spiral trail at Pilot Butte State Scenic Viewpoint — a cinder cone in the center of Bend — you can look out in all directions and see the grandeur of the high desert. Sunset is a special time, when you can see the silhouettes of the Three Sisters, Mt. Jefferson, Black Butte and Mt. Hood in all their glory. Among the landscape of juniper and sage, you can also feel the energy radiating from each outlying community, set against the Cascade peaks and bluebird sky. As a lifetime Oregonian who’s lived in Central Oregon for 11 years, I’ve learned that while Bend is the hub and heart of Central Oregon, the surrounding communities are the limbs that keep the region playing and working.
I often find all kinds of hidden adventures when I visit the handful of small towns that surround Bend, about a 30- to 45-minute drive in any direction. You’ll find rich urban, Western and wilderness experiences that don’t always make international travel lists. Three of my favorite towns are Redmond, Prineville and Tumalo — places where you’re sure to find new favorite eateries, museums, parks and trails. If you have 24 hours or more to spare, here’s my rundown of where to play, eat and stay in these high-desert hamlets.
20 minutes northeast of Bend, in the tri-cities triangle
This region is perhaps best known as the birthplace of American sport climbing at Smith Rock State Park, nine miles north of Redmond in the small town of Terrebonne. Redmond is also home to some other awe-inspiring natural areas for biking and hiking — most notably the paved Dry Canyon trail. Touted as the crown jewel of the Redmond parks system, the majority of this 3.7-mile trail is set aside as a nature preserve. Visitors can enjoy the pavilion, picnic tables, water fountains and a dog park. You can also play tennis, pickleball, softball and disc golf, and climb a high-angle route on the arched underbelly of a bridge.
In downtown Redmond, great dining options abound. Snag a seat on the patio at Wild Ride Brewing and order from their rotating selection of food carts. Classic pints like Phil’s Pils (named for the iconic Phil’s Trail network in Bend) and Nut Crusher Peanut Butter Porter are served at their taproom and production facility, a charmingly reimagined lumber-storage building. If you’re in the mood for gourmet wood-fired pizza, check out Grace and Hammer just around the corner, which tosses original-recipe homemade dough with all your favorite fixings. The restaurant is housed in a converted church, complete with stained glass and pitched ceilings.
In Redmond’s bustling downtown, book one of the plush rooms at the boutique SCP Hotel, which stands for “Soul, Community, Planet.” Enjoy the eco-friendly amenities, fair-trade pricing and cool aesthetic, with hallmark hipster Oregon touches like lush plants, antler sheds and river rock. If you aren’t looking for an overnight stay, you can still enjoy locally inspired small plates, seasonal craft cocktails and panoramic views of the Cascades from The Rooftop restaurant and bar. Or check out Provisions Market in the hotel lobby for grab-and-go, plant-forward food and drinks.
45 minutes northeast of Bend; the gateway to the Ochoco Mountains and John Day country
The best thing about Prineville is that it’s the site of the first Western homesteads and settlements in Central Oregon, and that pioneer spirit still resonates today. The Bowman Museum is worth the trip to check out the hands-on, family-friendly displays of the town’s early days as a lumber town. Find exhibits about logging, woodland firefighting and sheep farms, as well as replicas of a doctor’s office, a typical dining room and a bedroom — all filled with original local artifacts. (Admission is free, too.) Outside the museum, kids like to climb aboard the restored yellow caboose.
Next door is Good Bike Co., a gateway to everything biking in the region, especially the Ochoco trails and Lookout Mountain. In fall the annual Ochoco Overlander bike-packing event makes for the perfect outdoor long-weekend getaway. The bike shop is housed in a converted service station where visitors can stop in for bike and paddleboard rentals, repairs, and purchases or hydrate with a pint of beer on tap. Once you’ve got your bikes, head over to the pump track at Ochoco Creek Park, a sweet paved trail in a greenbelt along the creek. Families will enjoy a wooden-castle kids park, a skate park and tons of spots to picnic. If biking isn’t your thing, trade the handlebars for a set of clubs at two premier golf courses in town, Meadow Lakes and Prineville Golf Club.
Feeling rumbly in your tumbly? Sidle up to the counter and grab a burger at Tastee Treet, two blocks east of the Good Bike Co. You’ll find soft-serve ice cream, fries and the double-mountain burger challenge on the throwback diner menu here, plus gluten-free options and veggie patties.
Take your order to go and soak up the views at the top of Ochoco Wayside State Park, at the west entrance to town. Here you’ll find a killer sunset sitting atop a mesa overlooking all of Prineville.
Wanting first-class craft brews and pub fare? Crooked Roots Brewing — just north of the Bowman Museum — is an excellent spot for both (hello, thin, crispy stone-fired pizzas!), plus fire pits outside, an arcade and an indoor movie theater.
To get some rest and relaxation under the starriest skies in all of Oregon, you’ll want to book a campsite at Prineville Reservoir State Park. The park was designated as Oregon’s first International Dark Sky Park for its lack of light pollution and the exceptional quality of its night-sky viewing. Consider downloading a star-viewing app to your smartphone for a personalized stargazing tour. If you’re traveling on a budget, Prineville is home to some of the most affordable accommodations in Central Oregon including Rustler’s Inn, which serves up modern comfort along with rustic Western charm. Family owned for three decades, the inn offers a laid-back saloon vibe with unique amenities like old-fashioned phones, poster beds, unique wooden sculptures, antique furniture and faux fireplaces.
10 minutes northwest of Bend, a ranchers’ and farmers’ paradise en route to Sisters
Blink and you’ll pass the small town of Tumalo on Highway 20. Though you won’t find a single supermarket or shopping mall, you will find sprawling sagebrush and quirky outposts alongside the Deschutes River, as well as tons of biking opportunities on uncrowded pavement, dirt and gravel paths. Cline Buttes and Maston are favorite spots for mountain biking. Stop in at Backcountry Recumbent Cycles to get all the beta you need on local cycling routes and trails. After sweating it out in the high desert, you may want to sit in the cool waters of the Deschutes River, and Tumalo State Park is the perfect spot for a quick dip. Locals like to walk upriver and tube a short section that passes through the park (just follow the crowd). Water too cold? Have a picnic instead or walk the extensive trails.
Post-adventure, fuel up at The Bite — a locally owned collection of five food carts (offering tacos, sushi, Thai curries, pizza, hearty sandwiches and salads) with ice-cold craft beers, kombucha and cider available at the permanent outdoor tap station. Check out their lineup of live music in the summer. For something slightly more fancy, Tumalo Feed Co. across the street is a must for its legendary steaks, burgers and sandwiches, plus live music on the patio and a great “Howdy Hour” menu for smaller bites and drinks.
Tumalo State Park makes a perfect base camp for a Central Oregon visit — just make sure to book your campsite far in advance, since spots fill up fast. If you’re ambitious, it’s only a 20- to 30-minute road-bike ride to Bend. As the golden hour sets in, you might want to close out your day with a hike at Upper Tumalo Reservoir, 5 miles west of the campground, and search out one of many scattered trails or traverse the shoreline. Along the drive (or bike ride), you’ll catch epic views of genuine high-desert farmscapes with outstanding Cascade mountain backdrops.