Bend has breweries galore and Bachelor; Sisters its charming Old West architecture. But what makes Redmond destination-worthy? The city of approximately 36,000 is more often than not seen as a place on the way to your high desert adventure, an oversized mile marker indicating you’ve almost made it to your destination.

But I’m here to tell you to book your next stay in this often-overlooked town. A long weekend getaway in Redmond comes with all of the highlights you’d expect from Bend—breathtaking volcanic landscapes, award-winning beer, and an exceptionally walkable downtown. But unique features also define the area, like a 300-foot-deep canyon you can walk across or bungee-jump into, a network of lava caves that are open year-round, and a rooftop bar with a view of every notable mountain in the region.

On top of all that, Redmond is attracting a number of new businesses that will enhance any visit. Since 2020, the city’s core has gained a wood-fired pizzeria operating out of an old church, an artisanal butcher that serves outstanding sandwiches and draft beer, and a honky-tonk-style food truck corral with a cantina. Thanks to Redmond’s small-town status, no place ever feels mobbed, even during peak business hours—from brunch to nightcap.

So the next time you load up the car with hiking gear and river floats for a Central Oregon vacation, type “Redmond” into the GPS instead of Bend. Not only will you discover new attractions at bargain rates; it lops off 20 minutes from the drive.

THURSDAY NIGHT

Check In and Play DJ

Since Highway 97 slices through town, there are plenty of budget inns scattered from north to south for anyone who’s done driving for the day. But SCP Redmond Hotel (521 SW 6th St., Suite 100, 541-508-7600, scphotel.com/redmond) isn’t, on average, that much more expensive than the Motel 6 or Super 8. California-based Soul Community Planet, a sustainability-focused hospitality company that plants a tree for every stay, reopened the property in December 2019 following a two-year, $7 million renovation. Yes, timing was not on its side since the pandemic lockdown happened just a few months later, keeping would-be travelers at home. Which is why 2023 feels like the hotel’s true grand opening now that COVID emergency declarations have ended.

The days of darting through lobbies to avoid breathing the same indoor air as others are a thing of the past. Here, the grand foyer invites you to linger. There is a table that doubles as a chess board, pieces in place and ready for players. A pair of netted papasan chairs sit near an Audio-Technica turntable and extensive record collection. And there’s always a welcoming glow coming from the stone fireplace. In 1928, when the Redmond Hotel opened—then with the name “New” since it replaced the original fire-destroyed business—the collection of 49 rooms was billed as the finest overnight lodging east of the Cascades. The same may still be true to this day.

Search for a Sunset

Vale, a tiny town 12 miles from the Idaho border, is the first Oregon city westbound pioneers would encounter on their wagon route. Today, more than 30 murals on walls throughout the community document that migration, becoming their own attraction. You won’t find that many large-scale paintings in Redmond, but there is one stop on the Central Oregon Mural Trail (520 SW Evergreen Ave., visitcentraloregon.com) right across the street from the hotel. The “Greetings From” series is modeled after those colorful mid-20th century postcards by depicting the landscapes of and wildlife native to the region’s cities. Redmond’s mural stands out because it’s the only one portraying dusk, giving downtown an everlasting view of a Central Oregon sunset, with a blushing red sky just before it dims to purple.

Achieve a High-Altitude State of Mind

Grab a pre-dinner drink at Wayfarer Club (525 SW 6th St., 541-508-7600, scphotel.com/redmond/wayfarer-club), the hotel lobby bar, which transports you out of Redmond and into a rustic mountain resort. A full-sized canoe made of glossy blond wood hangs from the ceiling, while a pair of skis and a pickax adorn the walls. Though much of the décor says “high-elevation lodge,” you’ll be reminded of your high desert farming country surroundings anytime a flatbed piled high with hay bales drives by. No matter where you think you are, the cranberry mule is a refreshingly sassy fuchsia blend of Wild Roots vodka, demerara and ginger syrup with a peppy bite. I’m told that’s because Wayfarer makes the latter ingredient in house. “It’s extra gingery,” according to my bartender.

Eat Your Greens

It takes guts to run a vegetarian restaurant in Oregon cattle country. There are beef farms dotting the countryside, at least three butcher shops in town, and the livestock auction is just up the highway in Madras. But Redmond Hotel’s resident eatery, Terra Kitchen (509 SW 6th St., 541-615-8001, scphotel.com/redmond/terra), successfully swaps out ground chuck for eggplant in its Bolognese and piles pizzas with produce. Head chef Erin Behzadian sources as many of those ingredients as possible from local farms and the hotel’s rooftop plot. That means the menu is constantly changing with the seasons. No matter the month, the dining room will always feel like spring in Mr. McGregor’s garden thanks to its abundance of watering cans, clay pots and wooden planter boxes filled with live greens.

Work through the menu by ordering a couple of starters and at least one entree to share. Mid-April’s harvest rewarded with stocky grilled asparagus spears capped by a sunny egg and blazing-red Fresnos, a purple blood orange and milky burrata pairing, and risotto studded with visually electrifying greens: snow peas, mint leaves and grassy pea shoots. “It took me three days to shell all of those,” my server said. For that, I am forever grateful.

Breathe in Mountain Air

On night one, you need not venture from the hotel to find enough to do to stay occupied. A nightcap awaits right above your bed at The Rooftop (521 SW 6th St., 541-508-7600, scphotel.com/redmond/rooftop). On my visit, I was amazed to find plenty of open seats at the 1,500-square-foot indoor-outdoor bar, four floors up. A perch like this in Portland would be packed, but there were a few unoccupied sofas next to fire pits waiting for visitors. It was a front-row seat to Central Oregon’s best sky show: Broken Top, the Three Sisters, Mount Washington, and more. Order a charter yacht-worthy drink to pair with your similarly luxurious (albeit landlocked) view: a roasty and bitter yet smooth espresso martini.

FRIDAY MORNING

Get Stuffed With Gravy and Gossip

This two-story brick red home is one of several converted residences where you can find a fine meal in Redmond. Christie’s Kitchen (614 NW Cedar Ave., 541-923-8878, christieskitchen.business.site) is a no-frills breakfast and lunch joint—the kind of place where locals come to read the Bend Bulletin from the patio paper box or gather to dish the dirt. Eat hearty, because you’ve got a busy day of hiking ahead. Dense yet airy scratch-made biscuits smothered in peppery gravy are always a good choice here, and a half-order comes out looking as if the kitchen made a mistake and gave you a whole serving. Pair that with a side of one egg, over-easy. Those biscuits are good at sopping up both gravy and yolk.

Walk Across a Grand Canyon

Peter Skene Ogden State Scenic Viewpoint (Highway 97, Terrebonne, 541-546-3412, stateparks.oregon.gov) looks like little more than a rest stop when zipping by in a car. Sure, there are restrooms and truckers on break, but one of the most stunning views in all of Central Oregon can also be found here. The sign that greets you in the parking lot is jarring: “Warning Hazardous Cliff. Put your dog back in the vehicle!” In fact, notices are everywhere for a good reason. The 300-foot-deep Crooked River Canyon is just up the path, and there’s a shockingly short barrier between you and the bottom of that ravine. Anyone made weak-kneed and wobbly by heights should probably skip this landmark, but if you’re brave enough to walk along the ridge’s edge, you’ll get to see the Crooked River cutting through the jagged canyon as well as three beautiful arch bridges connecting the chasm’s two sides.

The first span built there in 1911 is the 460-foot-long Oregon Trunk Line Railway Bridge, and trains still come chugging across it more than a century later. In 1926, the completion of the Crooked River High Bridge allowed cars to get over the canyon. At 295 feet above the river, it was, at the time, the country’s highest single-arch span. Now, you can stroll across it to take in the sights since vehicles were rerouted to the neighboring Rex T. Barber Memorial Bridge, which is 535 feet long and the first cast-in-place concrete arch in the U.S. But wait! The canyon boasts one more record: It’s the site of the tallest commercial bungee jumping in North America, which the truly courageous can register for in May through October.

FRIDAY AFTERNOON

On the Rocks

Reunite with the Crooked River just a few miles south at Smith Rock State Park (Terrebonne, 541-548-7501, stateparks.oregon.gov), where the water meanders around the castlelike formation as if it were a natural moat. Located just minutes off the highway—it’s essentially Terrebonne’s rugged backyard—the 650-acre site is one of Oregon’s seven natural wonders, formed after a volcanic eruption covered the area in ash that eventually hardened. Wind and water worked their magic, creating majestic cliff walls, serrated spires and rounded pillars.

Though visitors hardly have to get out of the car to see Smith Rock, a world-class climbing destination, a hike is a must in order to truly appreciate the beauty of every peak and cranny. Despite its ominous name, the approximately 4-mile Misery Ridge loop isn’t as murderous as it sounds. A series of switchbacks at the front end of the trek will be strenuous, helping you gain elevation and great views while remaining safely on the ground (unlike the climbers dangling above). Once you reach the 350-foot-tall monolith named Monkeyface, which resembles a grinning chimp, you’ll wind downward along a steep path before connecting with a flat trail wrapping around the southern tip of the rock that returns to the starting point. The Oregon Parks and Recreation Department will be replacing Smith Rock’s pedestrian bridge this summer, cutting off access to Misery Ridge for a few weeks, so come with a backup route.

They Have the Meats

I’ve eaten the heralded fried bologna sandwich at Robert’s Western World. The Nashville honky-tonk’s stack of thinly sliced meat on Texas toast—served with a mini bag of Lay’s and a PBR as the “Recession Special”—is one of the country’s great, iconic sandwiches. The version at Sisters Meat and Smokehouse (308 SW Evergreen Ave., 458-899-5249, sistersmeat.com) is better. Founded in the town it’s named after in 2016, this butchery quickly developed a loyal local following and expanded to Redmond in April. Refuel post-hike with one of the six made-to-order sandwiches and a beer fresh from the tap. The bologna is stuffed with no fewer than four layers of meat browned to perfection, as well as cheddar, lettuce, tomato and onion. Turns out, this combo is the owner’s second-favorite item on the menu, coming in just behind the Reuben. You bet I know what I’m ordering on the next visit.

FRIDAY NIGHT

Follow the Redmond Tap Trail

There are no physical trophies for people who visit every brewery in Redmond, but the city’s travel bureau does promote the Redmond Taps Tour online and you can consider your reward the pub crawl itself. Here’s the route:

Start at Wild Ride Brewing (332 SW 5th St., 541-516-8544, wildridebrew.com). At nearly 10 years old, the Redmond elder statesman still boasts the liveliest crowd. The opening of the stop sign red-accented business was the jumper cable downtown needed for growth, and it was among the first to adopt a food cart pod model. Order this: Nut Crusher, a Reese’s Peanut Butter Cup in a glass, or Cole’s Light Lager, which snagged bronze at this year’s World Beer Cup.

The Cascade Lakes National Scenic Highway will take you to all sorts of great hiking trails as well as the Bend outpost for Cascade Lakes Brewing, making it an easy stop on the way back into town. The original 7th Street location (855 SW 7th St., 541-923-1795,cascadelakes.com) in Redmond isn’t as visible to traffic, but offers a similar experience—except for the park-style picnic shelter here, which provides more shade for outdoor drinking. The beer is hit or miss, so order This IPA and pray it wasn’t made on an off day.

The production facility for Kobold Brewing is a ways from downtown, so you’ll never drink amid the tanks at The Vault (245 SW 6th St., 541-504-9373, koboldbrewing.com), its intimate, low-key taproom. But that’s OK. The only company you need is that of the business’s beer-swilling namesake sprite, which hangs out next to the bar. The brews have improved since my last visit, but you can always play it safe by sticking to the stout.

Initiative Brewing (424 NW 5th St., 541-527-4380, iniativebrew.com) is the new kid in town, opening a pub four years ago inside what has to be a former modern-era bank considering the building’s dull brick exterior. But that façade belies the party inside. On a Friday night in spring, nearly every table was full with people ordering both beer and food. The shiny silver brewhouse sits just behind the bar, and see it here while you still can. If all goes according to plan, Initiative’s owners will move it to a new second location in Madras. Try the Snozzberry Cranberry Lime, a sour that’s playful and different from anything else you’ll find in town.

Feast on This

Inside Feast Food Company (546 NW 7th St., 541-923-0170, feastfoodco.com), it appears as though movers could’ve just swapped out the single-family home’s couch and TV set with dining room tables and chairs, creating some sort of underground supper club. But this 1940s ranch-style abode is actually an ordinary, above-board restaurant operated by Chris and Emma Leyden, who founded the brand as a food truck in February 2021 before upgrading to brick-and-mortar status at the tail end of 2022. That accelerated growth is anything but ordinary, which speaks to the quality of the cuisine. The offerings have since expanded and continue to feature hyperlocal ingredients—one side of the menu always gives a shout-out to the farms they source from. Order anything that’s jammed packed with local produce, like the chicken and gnudi, pillowy-soft ricotta dumplings that sing when served in a stock swimming with two kinds of squash (spaghetti and kabocha), baby kale and charred poblanos.

SATURDAY MORNING

Poached

Welcome to another converted house! One Street Down Cafe (124 SW 7th St., 541-647-2341, onestreetdowncafe.com) is a second red breakfast cottage with dishes that are slightly more elevated than the diner-style fare at Christie’s. Specials are advertised on a sandwich board outside the front door, which includes creative takes on a Benedict. During my visit, chipotles gave the Hollandaise a spicy twist, and tired disks of Canadian bacon were replaced with smoky sausage patties. All beverages—from the locally roasted coffee to the mango-peach mimosas—come in bowl-sized glassware; good news for anyone in need of a midmorning buzz.

Cannonball Run

Bendites can simply walk out their front doors and into the Deschutes River, which flows through the city. If you’re in Redmond, getting to the major tributary requires a ride in the car, but one that never lasts very long. A popular swimming hole is located about 15 miles north of town at Steelhead Falls (Terrebonne, 541-416-6700, blm.gov). The crescent-shaped cataract is surrounded by cliffs, making this the perfect location to jump in. While short, the half-mile hike down into the rimrock canyon offers enough gorgeous scenery to fill a feature-length motion picture. Layers of multicolored rock in the cliff walls tell a beautiful story about a disruptive geological past, and this blue-green meandering stretch of the Deschutes attracts anglers and birds of prey alike searching for a fresh catch.

SATURDAY AFTERNOON

Life’s a Picnic

The trail to Steelhead is narrow and bordered by some steep drop-offs, making it less than ideal for picnicking. Fortunately, Cline Falls State Scenic Viewpoint (7100 Highway 126, 541-388-6055, stateparks.oregon.gov), also along the Deschutes, offers plenty of room to spread out. On the way back through Terrebonne, make a pit stop at Ferguson’s Market (8150 Highway 97, Terrebonne, 541-923-0729, fergusonsmarket.com), a small grocery and deli that has everything you need for an al fresco meal, as well as an extensive inventory of cowboy hats. Once at the park, saved from its original fate as a gravel pit, you’ll find yourself wondering where the falls are. To get there, walk back toward the parking lot entrance, then veer left on a dirt path, crossing under the Highway 126 bridge. You’ll reach water gently cascading over a short basalt ledge, streams flowing through multiple crevices, which is Cline. Pick a rock in the wide-open viewing area and lay out your lunch.

Go Spelunking

This land was shaped by lava, and visual reminders of that dominate the skyline. However, some subterranean evidence of volcanic activity is accessible, like the Redmond Caves (Southeast Airport Way, 541-416-6700, blm.gov). This series of five chambers was formed some 80,000 years ago by molten flow from the Newberry Caldera. Now, you’re free to roam these hollows on Bureau of Land Management property near the airport. Claustrophobic? Afraid of the dark? Push yourself to the limits by slipping into the chilly murk, where a headlamp or powerful flashlight is necessary for navigation. Though not so well known as Bend’s seasonally operated Lava River Cave, this area is free of charge to explore and open year-round. But the lack of supervision also means these tunnels are sometimes used as a drinking den, as evidenced by the beer bottle caps and empty cans of Twisted Tea. Look past the occasional graffiti and get out before dusk, lest you accidentally crash the next below-ground boozer.

SATURDAY NIGHT

Become a Ginfluencer

Only open for three hours on Friday and Saturday evenings, carving out time for Gompers Distillery (611 SE Jackpine Court, #8, 541-588-2825, gompersdistillery.com) is nonnegotiable. Tucked away in a nondescript industrial park, the only sign that something special is going on at Redmond’s sole spirits producer is a pair of red velvet ropes outside the front door. Beyond the entrance lies a lounge fit for Oliver Warbucks, with tufted Chesterfield-style armchairs and a green marble bar all illuminated by a sparkling chandelier. Founded in 2012 by Michael and Jessica Hart, Gompers started as a ginmaker, putting the area’s abundance of juniper berries to good use, and later added vodka to the lineup. Sample those spirits alone as a flight or in classic cocktails, like a gimlet. Be sure to raise a glass to the distillery’s inspiration, Herman Gompers, Jessica Hart’s late grandfather, who survived the Holocaust—escaping capture twice—and went on to become a successful baker in California.

Boot Scootin’ Boogie

Perhaps I lacked company on the Redmond Hotel Rooftop because Blacksmith Public House (308 SW Evergreen Ave., 619-405-2589, blacksmithpublichouse.com) had just opened during my visit, and it appeared as though everyone in town turned out for the festivities. The old ironworkers’ shop is now three operations in one: a bar, a live music venue and a food cart pod. Inside, it looks like the owners dug up a neon-decorated segment of Nashville’s rowdy Honky-Tonk Highway and deposited it in Redmond. Outside, the scene is more family-friendly, as people gathered at tables to devour their food and children toddled around the half-circle of six concession stands. During Blacksmith’s debut, the top dish came from That Guy’s Bistro: a tri-tip “Filly,” whose meat and marinated mix of onions, mushrooms and red peppers coated in melted provolone came in flatbread—a perfectly acceptable alternative to a hoagie roll in this case.

SUNDAY

A Taste of Heaven

The first time I went to Grace and Hammer Pizzeria (641 SW Cascade Ave., 541-668-6684, graceandhammer.com), I didn’t even make it through the front door. A sign on the entryway was the bearer of bad news: “Sold out of pizza tonight!” I stood there a little stunned, but I had to admit that getting wiped out of pies was a testament to their quality. I made it my mission to return the next day at opening to understand why everyone in Redmond worships at the Pizza Church, which is the perfect way to close out your stay. Located in a former house of prayer built in 1912, the stained-glass art, cathedral arch windows, and tall spire all make this one of the prettiest places to eat in Redmond. But the pizza is what really elevates Grace and Hammer to “divine” status. The massive metal wood-fired oven produces crisp, crackery crusts, and the housemade béchamel may cause you to ditch red sauce for good.

Feed the Alpacas

The high desert stretch of Highway 97 will take you past plenty of farms with cows, horses and even a herd of longhorns. More unusual are the alpacas roaming the grassy roadside acreage of Crescent Moon Ranch (7566 Highway 97, Terrebonne, 541-923-2285, crescentmoonranch.com). The business raises camelids for their voluminous fleece, which is renowned for its softness and heat regulation. Inside the ranch’s Alpaca Boutique, you’ll find all sorts of items made with alpaca fiber—yarn, socks, ponchos. Also for sale are $5 bags of grain pellets. Buy one and get to feeding. A marked path takes visitors through the property, where hungry alpacas and their ticklish nuzzles await.

Top Scoop in Town

Sno-Cap Drive-In

1053 NW 6th St., 541-548-2343. 11 am-8 pm Sunday-Thursday, 11 am-9 pm Friday-Saturday.

There are plenty of unwritten rules for the American road trip. To that list I will add this: Any cinderblock building sporting the name “Drive-In” is worth a stop. Not only are you likely to find diner classics, like griddled burgers and club sandwiches, for less than $10, there’s bound to be an ice cream case stocked with local or regional brands whose flavors will take you back to your childhood. In Redmond, that place is Sno-Cap Drive-In, a local landmark painted in shades of retro-Wendy’s yellow and red. A sign on the ‘70s-style wood-paneled walls displays 18 varieties of Eberhard’s Dairy ice cream, which is made with locally sourced milk just a mile down the road. Order a scoop in one of three types of cones, or tackle a whole pint if you’re feeling really ambitious.

SUMMER SAVINGS

Sisters Meat and Smokehouse – Fried bologna sandwich $14

Gompers Distillery – Cocktails $12

Cave spelunking – Free!

This story appeared as part of Oregon Summer, our annual free magazine out now all over Portland. See where to pick one up here.