Trip Planner: Redmond

Smith Rock is a short drive and a must-see state park. Photo by Caleb Thomas.

Central Oregon’s oft-overlooked city is getting cool before our eyes

written by Sheila Miller

Not so long ago, downtown Redmond was crowded—but not in a good way. Thousands of vehicles traveling north and south on U.S. Highway 97 drove right through the middle of downtown on Fifth and Sixth streets. Semi trucks coughed plumes of diesel and horns honked all day—downtown Redmond a decade ago was not a place you lingered.

But ten years can mean a lot of change, and Redmond has made great strides. Today, this is a city center that has been reborn. There are vestiges of the old city—a Sears Hometown store still holds a prominent place in the downtown core and the Historic New Redmond Hotel is undergoing what may seem like never-ending renovations. But around the corner is a city-operated ice rink, Centennial Park with its green space at the center of downtown, and Evergreen Elementary reborn as a stately city hall.

You could come looking for the Redmond that was famous for having a polar bear at the gas station (the glass case is now empty), but why not explore the new version? Look closer—you’ll see the boom all around you as new businesses open, small shops thrive and downtown gets crowded again, this time with people.


One of the great benefits of Redmond is that the airport is here, which means you can get off a plane and have a locally crafted beer in your hand within fifteen (maybe ten) minutes.

Bend may get the attention when it comes to beer, but Redmond has a burgeoning scene of its own. Cascade Lakes Brewing, which started in 1994 and is among the oldest breweries in Central Oregon, got its start in Redmond and still has a brewpub and its production facility here. Since then, Silver Moon Brewing has moved its production facility to Redmond, and other breweries have popped up all over.

Start at Wild Ride Brewing on Fifth Street, which opened in 2014 and immediately became a vital part of the community. The tap room has a relaxed vibe, with garage doors that open up to a huge patio area. Instead of serving its own in-house food, several food carts have made their home in the parking area nearby. Grab a Shredtown Bowl, then pair it with a Nut Crusher Peanut Butter Porter and prepare the rest of your day. 

Swing a few blocks over to The Vault Taphouse, on Sixth Street. The taphouse serves primarily beers from Kobold Brewing, a recent addition to Redmond’s beer scene. Taster trays are $10 and you’ll get a wide variety of great flavors. From there, move two doors down to Proust Coffee for a perk up. This little coffee shop is small and spare, with a shelf of books to borrow on the wall and a very powerful weapon—liege waffles, crunchy on the outside with caramelized sugar throughout. Once you’ve recharged with a latte and a waffle, try another brewery—Smith Rock Brewing is also in the downtown core and has a cool
outdoorsy theme.

Initiative Brewing is in the process of opening a space that formerly housed a bank, and Porter Brewing with its cask-conditioned English ales and Dry Fields Cider are in the same complex on the edge of town.

Man cannot live on beer alone—we know, we’ve tried. Redmond has recently seen a bunch of Bend restaurants open outposts in town—The Hideaway, Baldy’s Barbeque, Croutons, Hola!, and the Bend Burger Co., though it’s called the Redmond Burger Co. here. They’re all good options, but this city has its own culinary stars.

Try Oishi, a sushi restaurant on Sixth Street with an extensive menu and a cult following. Or check out another downtown favorite, Diego’s Spirited Kitchen, which offers international food and killer margaritas. Diego’s is owned by the same people behind Madaline’s, on South Highway 97 (another great option).

Or you can combine dinner and a movie at the Odem Theater Pub. This longtime theater building sat empty before the new owners spruced it up, added beer taps and a full dinner menu and started showing first-run movies. Book a movie online, grab a burger and a beer and make a night of it.


Start your day with the short trip to Terrebonne and take in one of Oregon’s most beautiful places—Smith Rock State Park. It’s a fifteen-minute drive but well worth it to take in the spires, sheer cliffs and deep river canyons that look otherworldly. This is a must-visit if you’re a rock climber, but there are plenty of outdoor opportunities out here, including hiking and biking trails. Wear proper footwear, bring water and ascend the 5.5-mile Summit Trail for epic views and a true feeling of accomplishment.   

If you’d rather keep it close to town, meander through Redmond’s Dry Canyon. This park runs through the middle of the city, with a 3.7-mile trail, a disc golf course, Hope Playground—an accessible, inclusive playground that has structures for all ages and abilities—and the Maple Avenue Bridge, which has climbing routes on its arches.

Whatever outdoor adventure you pursue, it’s bound to jumpstart your appetite. Head back to Redmond and hit up Bogey’s for a burger and waffle fries or the Sno-Cap for a milkshake—this place is old school, and it’s still nearly always full. If you’re feeling the need to keep the health trend going, try a juice or smoothie from Just Cut Organic Juice Bar, which also has a gym inside.

Now it’s time to shop. Traverse Fifth and Sixth streets, the main section of downtown. Here you’ll find a variety of boutiques, like Willow Wild and Welcome Home, which has a whimsical selection of home and design products. And no stop in downtown Redmond is complete without a trip to Herringbone Books, an independent bookstore with a solid selection for everyone in the family. The bookstore focuses quite a bit on local favorites and hosts lots of events.

Head off the main drags and over to Fourth and Evergreen to check out  Beyond the Ranch Antiques, a 6,500-square-foot space chock full of antiques. Areas throughout the store are organized into themes, and there’s an outdoor “yard art” section. This is particularly a must-see if you’re at all into Western-style décor.

Finish your day at Red Martini Kitchen & Cocktails. The dinner menu is sophisticated and adventurous, and the martinis are the perfect end to a perfect weekend in your new favorite Central Oregon city.



Bogey’s Burgers

Red Martini Kitchen
& Cocktails

Just Cut Organic Juice Bar

Proust Coffee


Diego’s Spirited Kitchen


Eagle Crest

Panacea at the Canyon


Beyond the Ranch Antiques

Herringbone Books

Wild Ride Brewing

The Vault Taphouse

Odem Theater Pub

Smith Rock State Park

Dry Canyon


Where to Eat After Hitting the Slopes in Central Oregon


Oregon Weekend Getaway: North Willamette Valley


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