4 perfect days in Central Oregon

Situated on the eastern slopes of the Cascade Range, Central Oregon is known for outdoor adventure and craft beer fanaticism. In other words, it’s everything I need in a getaway.

I visited in early October, the peak of hiking and fresh-hops season, with the goal of soaking up the mountain and high-desert scenery, trekking bucket list wilderness trails, and sampling the legendary taprooms on the Bend Ale Trail, a self-guided tour of 30 breweries. Follow along on my 4-day itinerary to discover the best things to do in Central Oregon.

My outdoor adventure started almost as soon as I landed at Redmond Municipal Airport. I drove my rental car a mile south to the Redmond Caves, 5 easily accessible caves formed by volcanic flows of molten lava from the Newberry Caldera.

Without any special gear, I walked on the sandy floor about 50 yards into Cave 4, the cave closest to the parking lot, until my smartphone flashlight no longer dented the darkness.

It was easy to imagine this expansive cavern sheltering everyone from ancient tribes to delinquent teenagers. Sure enough, the Bureau of Land Management says these caves had been used by Native Americans for more than 6,000 years, but lately they’ve been targets for graffiti. Free; no restrooms.

After checking in to my downtown Redmond hotel, I walked 3 blocks and joined a lively late-afternoon crowd at Wild Ride Brewing. The dog-friendly, family-friendly taproom has indoor and outdoor seating, plus food trucks on-site. “Tasteski” tasting flights are served on skinny trays handcrafted out of half skis and tap handles (pictured). 

I especially liked the 3 Sisters American Red Ale, a hoppy amber-red ale with hints of caramel, and the Whoopty Whoop Wheat, a cloudy American hefeweizen with refreshing lemon peel on the finish.

If you enjoy dark beers, order the powerhouse Nut Crusher Peanut Butter Porter, which is also available in bottles and cans. “That’s the beer that took us off in the packaging world,” says head brewer Michael “Curly” White. “That beer changed the projection of Wild Ride.”

From Wild Ride, I walked to Cascade Lakes at 7th Street, feeling like I’d stumbled onto the set of Cheers. A pioneer in the Central Oregon craft beer movement, Cascade Lakes Brewing Company opened this classic brewpub in 1996, and the new ownership is taking it to new heights, which includes updating the menu.

Perhaps most impressively, the Rhine family—Bruce, Martha, and their 4 adult children—converted the business to a not-for-profit operation. General manager Andy Rhine says this move allows the business to offer employees better than industry-average compensation and donate all net profits to causes such as conservation and animal welfare. I capped my night here with a satisfying burger and fries and another superb tasting flight.

Dubbed one of the “7 wonders of Oregon” by the state’s tourism agency and known as the birthplace of U.S. sport climbing, Smith Rock State Park is a must-visit in Central Oregon. Even from the parking area, the jagged umber-colored cliffs towering over the Crooked River gorge are breathtaking.

The park’s signature hike, the 3.7-mile Misery Ridge Loop Trail, is considered challenging because of the steep switchbacks at the beginning (if you take the loop counterclockwise), but I didn’t find it overly strenuous. After the descent from Misery Ridge, the bulk of the hike is a flat riverside trail. I completed the trek in about 2 hours, passing at least a half dozen groups of rock climbers along the way. Day-use permit, $5.

After stopping at my hotel to shower, I drove 13 miles south to Tumalo to have lunch at The Bite, a festive bar and food truck pod with plentiful outdoor seating.

I was tempted by carts offering burgers, tacos, and pizza, but a tip from a local sold me on the seafood at NorthFresh. The Yuzu Ora King Salmon poke bowl (green onion, serrano pepper, pink Himalayan salt, and furikake seasoning) rivaled any poke I’ve had in Hawai‘i.

The bar has a rotating selection of 13 local beers on tap, along with ciders from next-door Tumalo Cider Co. and Bend Cider Co. But with a busy afternoon ahead, I washed my poke down with a delicious cup of … water.

To learn more about Central Oregon, I hightailed it another 13 miles south to the High Desert Museum in Bend. This unique institution is “a place-based museum,” says Director of Communications Heidi Hagemeier. “We tell the story of the region through the science, the history, the culture, and the art.”

The indoor-outdoor museum includes a reconstruction of a 1904 homestead complete with living-history interpreters, and a native-wildlife collection with river otters, porcupines, reptiles, and birds of prey.

If you visit during the summer, don’t miss the “Raptors of the Desert Sky” outdoor avian flight program. “There’s not many places where you can go to see 5 different species of raptors all flying right over your head,” says Jon Nelson, the museum’s curator of wildlife. Adult general admission, $17–$20. Show your AAA membership card to save 10%.

Bend is one of only 4 U.S. cities with a volcano within its city limits. Pilot Butte is like the city’s “north star,” a way for locals to orientate themselves. A mile-long nature trail to the summit of this ancient cinder cone is a popular workout, but I drove the paved road to the top. From the Pilot Butte State Scenic Viewpoint, I took in 360-degree views of Bend, the Cascades, and the high desert. Free.

For beer drinkers, Deschutes Brewery is hallowed ground. Owner Gary Fish helped launch the craft beer craze back in 1988, when he opened a small brewpub in downtown Bend and introduced locals to house-brewed Cascade Golden Ale, Bachelor Bitter, and Black Butte Porter.

Before heading to that now-iconic pub (the Deschutes Brewery & Public House) for dinner, I met up with Fish at his nearby brewery and tasting room on the banks of the beer’s namesake river to talk about Bend’s beer-town eminence. “Everybody is always trying to keep up with everybody else, so there is always something interesting going on at the breweries,” Fish said. “It's craft beer Disneyland to a certain extent.” 

Insider tip: Fish says the beer he drinks the most is his Bachelor Bitter, an English-style ale. “It’s also probably the one that’s the most popular with our locals,” he said. Brewery tours available; $10 (includes a pint).

Driving the loop counterclockwise, I passed stark black lava fields before climbing Santiam Pass and arriving at Clear Lake. A 5-mile hiking trail encircles the aptly named lake, but I headed straight to shore and picnicked on a log while watching kayakers paddle past fall-color reflections shimmering on the water. Free parking at Clear Lake Day Use Area.

With a full belly and a nurtured soul, I continued on the national scenic byway to the day’s main event: a 2.6-mile hike through a mossy forest to 2 spectacular waterfalls. The 120-foot “segmented” Sahalie Falls and 90-foot “block” Koosah Falls are connected by a serene, mostly flat trail that follows the cascading McKenzie River.

Though I’d snagged the last parking spot at the small Sahalie Falls Trailhead lot, I encountered only a handful of people on my hike. For 2 blissful hours, I was alone with the sound of rushing water, the scent of pine and red cedar, and my thoughts, which mostly consisted of daydreams about moving to Oregon. Free.

My final stop on the byway was the Dee Wright Observatory, which offers panoramic views across 65 miles of black lava rock from its 5,187-foot perch at the summit of the McKenzie Pass. As I climbed the stairs to the top of the moonscape-like lookout, I could understand why NASA had conducted drills with astronauts here in 1964 to prepare them for their lunar mission. Free.

The Rooftop lounge, for example, sources many ingredients for its small-plate and cocktail menu from its own organic garden. I visited at sunset and sipped a Midsommer Sangria (wine, mint, strawberry and basil, ginger-lime, and pomegranate) on the patio as the sky glowed orange behind the Cascade Range.  

For dinner, I moseyed downstairs to the hotel’s plant-forward restaurant. Terra Kitchen takes its farm-to-fork philosophy seriously: The menu includes a full page listing all the farmers, artisans, and purveyors it works with. The result is a riot of fresh, seasonal flavors.

I started with a mushroom pesto tartine of hazelnut, citrus arugula, Fresno chile, Manchego, mushroom duxelles, and kale pesto on locally baked bread. I continued the cornucopian theme with a vegetable paella featuring chorizo-seasoned cauliflower, snap peas, fennel, kale, whipped ricotta-chèvre, saffron rice, and romesco. My taste buds tingled until bedtime.

Bend’s picturesque riverbend area is best explored on 2 wheels, so I rented a town cruiser from The Hub Cyclery and charted a 6-mile loop around a plethora of urban parks fronting the Deschutes River. The route also passes through the Old Mill District, home to shops, restaurants, tasting rooms, and Hayden Homes Amphitheater, Oregon’s largest outdoor concert venue. City rental, $30 a day or $10 an hour.

For my last meal before flying home, I decided to Bend it like Belgium at Monkless Belgian Ales. The outdoor deck perched on a rocky ridge overlooking the river and amphitheater had caught my eye during my bike ride.

Owner Robin Clement says summertime draws a lot of diners in bathing suits. “It’s like a freeway on the river with all the tubers and stand-up paddlers,” she says. But this is no mere novelty joint: The Belgian-style grub (frites, mussels, waffles, schnitzel, etc.) and beers here are the real deal. In 2020, it was named “Midsize Brewpub of the Year” at the annual Great American Beer Festival in Denver.

• The mindfully designed 49-room SCP Redmond Hotel is the place to stay in Redmond. For every stay, the hotel donates the cost to plant a tree to reforestation nonprofit One Tree Planted. Rates start at $149.
• McMenamins Old St. Francis School Hotel is a lively downtown Bend spot with a pub, a brewery, a movie theater, and a Turkish-style soaking pool. Rates start at $165.
• A short walk to downtown Bend, the 17-room boutique Wall Street Suites has full kitchens and earns raves for its comfortable beds. Rates start at $179.
• In Sisters, the romantic Craftsman-style FivePine Lodge and Cabins, adjacent to the popular Three Creeks Brewing Company, offers complimentary evening beer/wine reception and bicycle rental. Rates start at $169.

There are nonstop flights to Redmond Municipal Airport from Denver, Phoenix, Salt Lake City, and Seattle, as well as 5 California cities: Burbank, Los Angeles, Palm Springs, San Diego, and San Francisco. 

Central Oregon is a year-round destination. The best time to visit is September, when whitewater-rafting outfitters are still running, and early October, when temperatures are mild and the leaves are turning.

That’s also fresh-hops season, when brewers are working with locally grown hops that haven’t been dried or processed. “That gives the beer a unique flavor that you really can’t get at any other time of year,” says Deschutes Brewery’s Gary Fish.