A quick 20-minute drive north from Bend leads to the former rural outpost of Redmond, Oregon. While its slightly warmer climate still hosts family farms and ranches on its outskirts, the growing city has developed a revitalized downtown area filled with shops, entertainment, and eateries. Driven by Central Oregonians seeking affordable housing or more space to expand, Redmond is shedding its rural image for a more vibrant urban experience.

Many visitors to the area know Redmond as the location of the airport and fairgrounds or as the last city before Bend on the drive south for vacation. However, in the last two decades, the city has begun to position itself as a true Central Oregon destination. Although you can still one-stop shop at national chain stores just south of town, downtown’s charming boutiques and flavorful eateries are where the action lies.

Geographically, Redmond has Highway 97 running north-south through it, with Terrebonne to the north, Bend to the south, Prineville to the east, and Sisters to the west. The SCP Hotel and Odem Theater Pub anchor the city center, which consists of 5th Street and 6th Street and their cross streets just north of Highway 126. As you move outward from downtown, older houses become newer subdivisions, which turn into farms and ranches encircling the city. And like most Central Oregon cities, public parks and trails are a constant presence throughout.

Start your day with a caffeinated beverage from Tite Knot Craft Coffee, just a few blocks west of downtown. Consistently voted best coffee in Redmond, the coffee cart and outside seating area offer homemade baked goods and coffee concoctions brewed hot or cold. If you prefer to sip your coffee in the heart of downtown, head to Junction Roastery and Social Club and hang out in their welcoming space inside the restored Patrick Building. Their old-fashioned, hospitality-first mentality invites you to visit with friends, new and old, while sipping freshly roasted coffee.

If you prefer to have your morning cup of joe on the go, consider people-watching at Centennial Park, located one block west of 5th Street. Families favor the park during the hot summer months for its Centennial Spray Park splash water feature. If you want to get some morning exercise, head over to the Dry Canyon Trail, where, if you’re early enough, you might see mule deer, coyotes, or rabbits. The aptly named paved trail and surrounding area extend approximately eight miles just west of downtown and are accessible to most users, including leashed dogs.

Afternoons in Redmond are made for shopping at local boutiques and lunching with friends. Specializing in cowboy-chic attire, the Desert Prairie Boutique, located in a century-old bank building, welcomes shoppers with a friendly smile and an extensive selection of women’s clothing and accessories. Make sure to check out their selection of Redmond and Oregon-specific items. If you haven’t had enough shopping, stay on 6th Street and stop by Willow Wild. Specializing in both current women’s fashion and unique Redmond gifts, Willow Wild caters to every style. Also on 6th Street, Cares & Whoas Glamour Ranch Décor & Gifts offers something for everyone. Try on a pair of cowboy boots, buy something Western-themed for your home, or treat your four-legged friend with a gift from this lifestyle boutique.

Redmond is known for its Mexican food, and one of the top offerings is Xalisco Latin Cuisine. When visiting this family-owned eatery specializing in New Mexican cuisine, try the Ahi Tuna Tostadas or the scratch-made corn tortilla tacos, which were voted the sixth best in the United States on Yelp.

If you came to Central Oregon to sample craft beer, Downtown Redmond has you covered. Initiative Brewery opened in 2019 with a fantastic selection of craft beers and a commitment to providing scratch-style pub food made with premium ingredients. Choose a beer from the chalkboard, and if you’re feeling hungry, pair it with an Initiative Burger. The burger is a delicious representation of Oregon’s cuisine, complete with a bun from Big Ed’s Bakery in Bend, Tillamook Cheese, grass-fed beef, and local veggies. If you want to try other beers, head to Kobold Brewing The Vault for an IPA, Pilsner, or Stout. This family-friendly brewery hosts evening events such as Bingo and Trivia Nights to keep you entertained while you enjoy a cold brew. The quintessential Central Oregon experience features an extensive craft beer list, outdoor seating, and a lineup of food carts daily at the Wild Ride Brewing Tap Room. Be sure to try the award-winning 3 Sisters American Red Ale and see what all the fuss is about.

A few close excursions above and below ground include Cline Falls State Scenic Viewpoint and Redmond Caves Recreation Site. Cline Falls offers a respite from the hot summer sun with swimming and fishing in the Deschutes River. Picnic tables are situated on the cool grass beneath shady trees, providing a relaxing space for lunch. If the day starts to heat up, consider heading underground to explore the Redmond Caves. Located near the Redmond Municipal Airport, the caves comprise a set of five distinct caves that Native Americans have used for over 6,000 years. The caves, formed by volcanic flows of molten lava from the Newberry Caldera, are preserved in their natural state. So, be sure to bring a friend and three sources of light and follow Leave No Trace principles.

As the sun begins to set over the high desert, Redmond offers a variety of exceptional, unique dining options. In the heart of downtown Redmond, Terra Kitchen is located within the renovated SCP Hotel. Walking by, you wouldn’t expect to discover a Mediterranean-style restaurant, rooftop garden, or rooftop bar and dining area. Terra Kitchen sources ingredients from local farms and SCP Hotel’s rooftop garden to serve patrons blue zone-inspired dishes. I highly recommend enjoying dinner with a view from The Rooftop restaurant, Redmond’s only rooftop restaurant with panoramic views of the Cascade Range. Handcrafted cocktails and a tapas-style menu also include ingredients from the rooftop garden. If you’re in the mood for a USDA Prime Steak, head to Brickhouse Redmond. Also serving fresh seafood and pasta, Brickhouse pairs its meals with an exceptional ambiance. And don’t forget to save room for one of their unique, delicious desserts, such as Blueberry Cannoli. 

For those looking to enjoy a game with their food, try The Hideaway in Redmond. The staff at The Hideaway combines a sports-oriented atmosphere with high-quality food and gourmet cocktails. Visit the tavern for the televisions and sports channels, but stay for the 22 beers on tap. The Hideaway also offers a fantastic brunch and Central Oregon’s “Best Bloody Mary.”

For artists, musicians, and music lovers, Redmond has you covered, too. Art & Music is the go-to place for artists and musicians to acquire necessary supplies or try out new gear. Their enclosed guitar room lets musicians test-drive a Fender Telecaster with a JHS Chorus pedal and Vox AC 15 amp. They also offer art and music classes for those wishing to broaden their repertoire. If you’re seeking additional art instruction for yourself or your kids or would like to host an art party, call Northwind Art Studio.

If you still have some energy left from your Redmond experience, check if High Desert Music Hall has a band performing. The beautifully repurposed, 9,000-square-foot former church features a main stage, a lounge with a full bar, and an upstairs VIP balcony area. By enhancing its food, fun, and fashion offerings, Redmond challenges Bend as a Central Oregon destination.

Odem Theater Pub; 349 SW 6th Street, Redmond; (541) 425-1850; odemtheaterpub.com. Movie times vary. 

Tite Knot Craft Coffee; 706 SW 10th Street, Redmond; (541) 526-5568; titeknot.com; open Monday through Friday from 6 a.m. to 4 p.m. and Saturday and Sunday from 7 a.m. to 4 p.m.

Junction Roastery; 708 SW Deschutes Avenue, Redmond; junctionroastery.com; open daily from 7 a.m. to 4 p.m.

Dry Canyon Trail; visitredmondoregon.com/attractions/dry-canyon-trail.

Desert Prairie Boutique; 404 SW 6th Street, Suite 100; (541) 527-1887; desertprairie.com; open Monday through Saturday from 10 a.m. to 5:30 p.m. and Sunday from 11 a.m. to 4 p.m.

Willow Wild; 321 SW 6th Street, Redmond; (541) 527-4320; shopwillowwild.com; open Monday through Saturday from 10 a.m. to 6 p.m. and Sunday from 11 a.m. to 4 p.m.

Cares & Whoas Glamour Ranch Décor & Gifts; 498 SW 6th Street, Suite 101, Redmond; (541) 645-3908; caresandwhoas.com; open Monday through Saturday from 10 a.m. to 5 p.m. and Sunday from 11 a.m. to 4 p.m.

Xalisco Latin Cuisine; 3835 SW 21st St., Suite #105, Redmond; (541) 923-3943; xalisco-latin-cuisine.restaurants-world.com; open daily from 11 a.m. to 9 p.m.

Initiative Brewing The Hub; 424 NW 5th Street, Redmond; (541) 527-4380; initiativebrew.com/the-hub; open Sunday through Thursday from 11 a.m. to 8 p.m. and Friday and Saturday from 11 a.m. to 9 p.m.

Kobold Brewing The Vault; 245 Southwest 6th Street, Redmond; (541) 504-9373;  koboldbrewing.com/the-vault; open Monday through Wednesday from 11 a.m. to 9 p.m., Thursday through Saturday from 11 a.m. to 10 p.m., and Sunday from 11 a.m. to 8 p.m.

Wild Ride Brewing; 332 SW 5th Street, Redmond; (541) 516-8544; wildridebrew.com; open daily from 11 a.m. to 10 p.m.

Cline Falls State Scenic Viewpoint; 7100 OR-126, Redmond; (800) 551-6949; stateparks.oregon.gov/index.cfm?do=park.profile&parkId=30; open for year-round day use. 

Redmond Caves Recreation Site; SE Airport Way, Redmond; (541) 416-6700; blm.gov/visit/redmond-caves-recreation-site; open daily from 7 a.m. to 7 p.m.

Terra Kitchen in SCP Hotel; 521 SW 6th Street, Redmond; (541) 526-3608; scphotel.com/redmond/food-drink/terra; open Tuesday through Thursday from 4 p.m. to 8 p.m. and Friday and Saturday from 4 p.m. to 8:30 p.m.

The Rooftop in SCP Hotel; 521 SW 6th Street, Redmond; (541) 526-3608; scphotel.com/redmond/food-drink/rooftop. Visit their website or call for opening hours and to make reservations. 

Brickhouse Redmond; 412 SW 6th Street, Redmond; (541) 526-1782; redmond.brickhousesteakhouse.com; open Tuesday through Saturday from 4 p.m. to 9 p.m. and Sunday and Monday from 4 p.m. to 8 p.m.

The Hideaway Redmond; 507 SW 8th Street, Redmond; (541) 526-5989; hideawaytavernredmond.com; open Monday through Thursday from 11 a.m. to 10 p.m., Friday from 11 a.m. to 11 p.m., Saturday from 8 a.m. to 11 p.m., and Sunday from 8 a.m. to 9 p.m.

Art & Music; 232 SW 5th Street, Redmond; (541) 527-4426; artandmusicredmond.com; open Tuesday through Friday from 11 a.m. to 6 p.m. and Saturday from 12 p.m. to 4 p.m.

Northwind Art Studio; 515 SW Cascade Ave., Suite 5, Redmond; (541) 508-9662; northwindartstudio.com.

High Desert Music Hall; 818 SW Forest Avenue, Redmond; (541) 527-1387; highdesertmusichall.com.