: Crooked River by Arian Stevens

5 Guided Adventures in Central Oregon

Adam Sawyer , Guest Author
March 6, 2019

The word “adventure” is synonymous with Central Oregon — from fly fishing and single-track mountain biking to exploring long-lost artifacts and scaling rocks at the birthplace of American sport climbing — all with an Instagramable landscape as a backdrop. There’s so much to discover here that you should definitely take the time to explore it on your own terms. But connecting with a local expert can add a layer of depth, comfort, and peace of mind to the experience. A great guide or outfitter brings hard-earned knowledge and a combination of traits that are difficult to come by: fun-loving but professional, with expert-level insight and the ability to entertain while educating. They’re a rare breed that can help elevate your overall adventure experience from satisfactory to sublime. Here are five top Central Oregon trips to take with a guide.

Crooked River by Arian Stevens

1. Fly fishing of the gods

Standing knee-deep in the Crooked River is a bucket-list experience for anyone that has ever cast a dry fly. The stream is known as one of the most prolific trout fisheries in Central Oregon. You can fish for a variety of trout here all year, but spring is a splendid time to take advantage of the river’s hatches. Hook Fly Shop knows which bends in the river are best. Newer to fishing and afraid of causing injury with an ill-fated cast? They’ve got you. Fly-fishing master who is one with the water? They’ve got you too. Their full-service, private outings run the gamut from half-day trips to lunch-fueled, full-day excursions. Gear is included, from waders all the way down to the flies.

Smith Rock by Tyler Roemer

2. Climb the rock that started it all

Central Oregon’s iconic Smith Rock, in Terrebonne, is one of the most strikingly beautiful and explorable geological formations in the state. It also happens to be the birthplace of American sport climbing. While Smith Rock is accessible year-round, spring is an optimal time to visit for fair-weather climbers. For beginners young and old, Smith Rock Climbing Guides can get you geared up and show you just how fun climbing is while teaching you the basics. For intermediate and advanced climbers, this operator is the only one permitted to guide all areas of Smith Rock State Park. Whether you want to introduce yourself to this adrenaline-fueled sport or sharpen your multi-pitch skills on Monkey Face, these guides literally have your back.

An iconic Central Oregon landscape, courtesy of Bend Photo Tours

3. Catching the light with a photo tour

Who doesn’t want to capture, interpret and share such a ruggedly beautiful landscape — be it in song, with paint or a photograph? Thanks in large part to smartphones, we have all found the photographer’s soul within us. Whether you just want to know where and how to take the best shots possible or elevate your photography to the level of fine art, an outing with Bend Photo Tours can help you draw out your inner Ansel Adams. The guides will take anyone with a digital SLR (single-lens reflex) camera and tripod out to some of the top spots to photograph in Central Oregon’s high desert, either on foot or via automobile, snowshoe, cross-country ski or even helicopter. Forget Instagram envy — you’ll be living the dream and shooting it, too.

Crooked River Canyon Scenic Bikeway, by Russ Roca

4. Pedal-powered adventure

If you like getting around on two wheels, at some point you’re going to want to find yourself in Central Oregon. The rolling landscape invites new or intermediate riders to explore the Crooked River Canyon Scenic Bikeway on a road bike. Experts may take on the exhilarating singletrack of Lookout Mountain — the highest point of the Ochoco Mountains, at 6,900 feet — in just 11 miles. Good Bike Co., based in Prineville, is a go-to option for all facets of gearing up and leading the charge on any of these epic rides. If you happen to be built of muscle and grit, their 4-day, 220-mile Ochoco Overlander bikepacking trip during the fall takes hardcore riders through the Ochoco National Forest, traversing 18,000 feet of elevation with catered meals, local beer, fishing opportunities at campsites and gear support along the way. 

Fort Rock Homestead Village Museum, courtesy of the Oregon Film Office

5. Take more than a few steps back in time

Fascinating human and geological history walk hand in hand at Fort Rock Homestead Village Museum in the town of Fort Rock, roughly 65 miles south of Bend. Fort Rock Cave, near Fort Rock Natural Area, is a designated National Heritage site, with visitor-friendly artifacts on hand to help tell the stories of Oregon’s rich cultural heritage. From the 9,000-year-old Fort Rock sandals to the turn-of-the-century homesteaders, visitors can revel in a number of old-timey eras — all with a backdrop of an imposing basalt feature that was once a lake bed, with its own endless stories to tell. The Fort Rock Museum offers guided history tours that, thanks to the work of the Fort Rock Valley Historical Society members and volunteers, help bring many of those accounts to life. Plan accordingly, as guided group tours begin in May and run through October and are expected to fill quickly.

Summer concert, courtesy of Les Schwab Amphitheater

When you go:

The adventure doesn’t stop when your tour is over. Time your guided tour with one of these annual events, among others in Central Oregon. There’s always something happening here.  

Bend Concert Series (Memorial Day through mid-September, Bend)

Sisters Rodeo (June)

4 Peaks Music Festival (June, Bend)

Sisters Outdoor Quilt Show (July)

Newberry Event Music/Arts Festival (July, La Pine)

Deschutes County Fair (late July-early August, Redmond)

Sunriver Music Festival (August)

Art in the High Desert (August, Bend)

Sunriver Art Fair (August)

Sisters Folk Festival (September)

Trip Ideas