Outward Bound in the City: Central Oregon’s 5 Best Urban Hikes

Hiking in Central Oregon can take you deep into the wilderness, far away from worry and stress. But sometimes all you need is a quick break from reality…just a half hour or so outside in nature, on a trail, alone with your thoughts (or with your dog, husband and two kids.) There are hundreds of hikes and trails available in and around Bend, Oregon and Sunriver, Oregon. These “Urban Hikes” are the perfect remedy to slow down our all-too-busy lives.

Pilot Butte State Park in Bend, Oregon

Pilot Butte Trail

Pilot Butte State Park, Bend
Two miles roundtrip | Easy
More than a century ago, Pilot Butte served as a beacon of sorts, guiding wagon train travelers to the Bend area and a manageable crossing of the Deschutes River, said to be located around the area of Farewell Bend Park. Today the dormant cinder cone is a year round destination for Bend residents and visitors who seek out this urban hike. Signage on Hwy. 20 guides visitors to an ample parking area and large park complete with playground area for young visitors. From there follow the signs to the trail head at the base of the cone.

Take a moment to survey the names and ages of the men and women, as well as boy and girls, who ascended the steep spiral path in record setting time. Set your stopwatch and track your progress to get an appreciation of their accomplishments. Follow the well maintained walking trail as it circles the butte. It’s a roughly 1 mile climb to the summit which rises some 500 feet above the surrounding terrain. From the top you can enjoy panoramic views of the Cascade Range to west, the Ochocos to the East and Smith Rock State Park to the north. Catch your breath and double back the way you came. If you’ve worked up an appetite, consider dropping by the namesake Pilot Butte Drive-In just across the street for a milkshake and burger that are second to none, after all this is an urban hike.

Deschutes River on the River Trail in Bend Oregon
View from the footbridge on the Deschutes River Trail.

Deschutes River Trail/Bill Healy Loop

Farewell Bend Park, Bend
Three miles round-trip | Easy
Thanks to the shared efforts of many community members and the leadership of the Bend Park District, Bend offers multiple places along Deschutes River corridor for visitors to hike, bike and play. Foremost among those is the popular loop from Farewell Bend Park at the Bill Healy Bridge to a footbridge roughly 1.5 miles upstream.

Formerly an out and back trail, the park district closed the loop, so to speak on this trail, shortly after construction of the Healy bridge. Today walkers can start on either side of the Healy Bridge and hike upstream into a narrowing canyon that is marked by soaring ponderosa pines along the river banks and steep lava tuff walls.

Keep your eyes open for eagles and osprey and other wildlife that make the Deschutes River their home. While hikers can and often do turn back before the bridge, it’s well worth extra steps. When you reach the bridge pause for a minute and contemplate that you are still standing inside the city limits of Bend as water rushes under your feet.

Dry Canyon Trail

Four-mile round-trip | Paved, Easy
Redmond isn’t blessed with all of Bend’s geographic diversity or riverfront access, but the area is not without its natural attributes — one of the most notable of which is the Dry Canyon Trail.  The four-mile paved pathway meanders from the so-called Spud Bowl area near Redmond Senior High north toward the city’s wastewater treatment plant. Since it opened more than a decade ago, the trail has become a popular destination for residents and visitors, providing a perfect backdrop for an afternoon stroll. As the name implies the trail is framed by lava cliff walls that once hemmed in an ancient river, the bed of which forms the general trail route. There are several access points, the most popular and accessible of which is found at Redmond’s Bowlby Park, about a mile north from the trail’s southern terminus.

Shevlin Park Trail

Tumalo Creek Trail (2.5 miles) Loop Trail (6 miles) | Moderate
The crown jewel of Bend’s park system, Shevlin is host to a variety of activities from wedding and family fishing at Aspen Hall to picnics, trail running and even mountain biking. The expansive forested park is open year round but best enjoyed from late spring through early fall when the long shadows of the soaring Ponderosa pine trees, left mercifully intact during Bend’s long ago logging frenzy, create an oasis for runners and hikers seeking to escape the midday sun.

Shevlin Park near Bend, Oregon

If you do overheat, relief is as close as a quick dunk of your head in the icy waters of Tumalo creek that rush down from the Deschutes National Forest  toward the junction with the Deschutes River below Bend. Located just west of Bend, visitors will find ample parking at park’s main entrance just beyond the bridge over Tumalo Creek. Runners and bikers can also try the small parking area in the Shevlin Commons neighborhood which offers quick access to a bike and runner friendly spur that follows the ridgeline through the Awbrey Hall burn area before dropping into the forested park and into the adjoining national forest.

Whychus Creek Canyon Trail

Six miles (out and back) | Intermediate

Like the Shevlin Park route, this trail isn’t technically “in-town” but it’s well worth the short jaunt down Elm Street from downtown Sisters. Located about four miles from the bustling Western themed storefronts, the trailhead is just off Highway 16 on the road to Three Creeks Lake. The out-and-back route follows Whychus Creek as it tumbles down from the shoulders of the Cascade Range, and includes waterfall views. The hiking-only trail is dog friendly and winds through a second generation pine forest and into the sub-alpine Manzanita. The trail includes some light scrambling over a basalt flow and down some relatively steep ascents and descents around the river, but isn’t beyond the technical abilities of most moderately fit hikers. The entire trail is a six-mile roundtrip, but trekkers can turn back wherever they like – the second waterfall at mile two making a good spot. If you’ve made good time and have a few minutes to spare, you can take a load off at the Three Creeks Brewing in Sisters where a Knotty Blonde ale and a heaping plate of Black Butte nachos are a great way to finish any afternoon.

Trail Running Tips From Central Oregon Ultrarunning Champ

max king trail running 3
Photo by Paul Nelson

The last job you’d expect a Cornell University grad with a Chemical Engineering degree to be doing is selling footwear. For Max King, working at the FootZone, a specialty running shop in downtown Bend is a perfect fit. The runner, best known for crushing ultramarathons as well as dominating short distance trail races, is in his happy place when he’s working, coaching, raising his two kids and running in Bend.

King runs ultramarathons in less time than it takes you to binge-watch half a season of your favorite show on Netflix. In November 2014 he set a new American record at the IAU [International Association of Ultrarunners] World Championships in Qatar. He crossed the finish line for the 100K in 6 hours and 27 minutes… I’m exhausted just typing that.

King trains in Central Oregon throughout the year. Because he runs short distances and long distances on pavement and dirt, I knew he’d have some great insight to share with others looking to get out and run on the High Desert.


What terrain does Central Oregon offer runners?

It’s a huge variety but what I would say we’re best known for is the mountain bike network of smooth, sweet singletrack. Smith Rock is a huge draw as well to a number of ultrarunners looking for something quintessentially Central Oregon.

What’s your go-to trail for a short run?

I have the (Deschutes) River Trail right out my front door for those. No traffic, a great surface, and great scenery too.

What about those long training runs?

For something longer you have all the trails right around Bend like the River Trail and Phil’s Trail. Usually I’ll want something hillier so I’ll drive to Smith Rock/Grey Butte, Green Lakes/Soda Creek, or Black Butte to get some real vertical in.

Favorite part about running on the High Desert?

I think the best thing about it is the weather for the long runs we get to do. It’s not a lot of fun to go for a long run and be soaking wet in the first 10 minutes, over here that rarely happens. The wide-open expanses and scenic views of the snowcapped peaks don’t hurt though either.

Max King trail running
Photo by Jill Rosell

Pavement or Dirt?

Dirt is definitely more enjoyable for me, but sometimes is nice to hit the pavement for something up-tempo and a little quicker.

How does the Central Oregon scenery enhance your running experience?

It definitely helps with the long distances. I always like running around Awbrey Butte on the River Trail. Coming around the north side you get the expansive views of all the mountains. It’s always so inspiring.

Any hidden gems for running in Central Oregon?

Taking off through the woods with no trail underfoot. I think something that a lot of people overlook is just the cross country running that’s available in Central Oregon. The wide-open forests allow you to just take off cross country. You do have to be more prepared with a map, compass, and/or a good sense of direction to pull this off, so it can obviously be more risky.

Advice on what to wear?

The best advice I can give is, be prepared with an extra lightweight wind jacket. They’re easy to carry in a pocket or pack when you’re out on the trail and such a life saver in weather that turns on you. I can’t tell you how many times a jacket like that has saved me.

Favorite place to get a beer in Central Oregon after a long run?

Crow’s Feet Commons. I love the atmosphere of Bikes, Skis, Beer and Coffee. They have a great mix of beer and cider on tap and they always have a thick, dark stout on nitro.