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The Story of Phil’s Trail, A Singletrack Mecca in Bend, Oregon

Built by Phil (and Bob, Paul, Jimmy, Ben, Kent, Eric, Cody, Mike & more)

When I was 10 years old, my dad and I drove out Skyliners Road to ride bikes with an old guy who wanted to show us a trail he’d built. The singletrack was new and barely ridden, but it was great fun, with swooping turns through a beautiful canyon. On the way home, I remember thinking, “Awesome trail, but nobody is ever going to ride waaaay out there, old man.”

The year was 1985, and that old man was Phil Meglasson. If you’ve ever ridden a mountain bike, by now you’ve probably guessed that trail was Phil’s Trail.

The group that started it all in 1979
THE PIONEERS OF 1979: John Bifield and Kate Heber (far right) owners of Bend’s first mountain bike retailer Century Cycles, are joined by friends for a ’70s summertime tour on clunker bikes.

Today, the Phil’s Trail network is one of the most popular trail systems in Oregon and is key to the outdoor lifestyle Bendites hold dear. But back in ‘85, there weren’t many purpose-built mountain bike trails anywhere—after all, MTBs had only been around since 1978. The few trails that did exist around Bend were wilderness hiking trails much farther out or town trails on then-undeveloped Awbrey and Overturf buttes.

So how did a game trail beget a singletrack mecca? What inspired the trail names that have become part of the Bend mountain biking vernacular?Afterall, what is a Storm King? And what does C.O.D even mean? What’s the tale of Phil’s Trail?

3 mountain bikers riding at Phil's Trail
Between K.G.B. and Marvin’s Garden, Nola Stryker, Corey Schmid and Lev Stryker ride the twisting terrain. | Photo by Katie Sox

The Visionaries

In 1984, Bob Woodward—who would later become a mayor of Bend—came upon a deer trail through a canyon, and he and his friend Phil Meglasson began making “improvements.” Meglasson had moved to Bend in 1977 for U.S. Geological Survey work to catalog existing roads and trails. His encyclopedic knowledge of every goat track in the region is attributed to his avant-garde use of a bicycle to do what had previously been done on foot. “Back then, the U.S. Forest Service said you could ride your bike anywhere you wanted in the forest. So if you just rode the same way four or five times, you’d have yourself a trail,” he said. “We didn’t use tools. We just rode our bikes through the woods. At that point there were so few people around that the Forest Service didn’t really care.”

A few years later, Jimmy Terhaar created Middle Phil’s (née Jimmy’s), following a fire break from Heater Rock at the top of the canyon to the next road west, where Whoops now ends. Then, in 1990, pro racer and MTB Hall of Famer Paul Thomasberg would take the trail even farther west. Upper Phil’s (originally called Paul’s) became the most difficult trail out there, and not by accident. “You gotta learn to ride hard sh**, you know? I needed that stuff. There was a selfish element to it,” said Thomasberg. At that year’s Mountain Bike World Championships, he finished fourth in the cross-country race and third in the downhill discipline, a combined feat that has never been matched.

Phil Meglasson rides at Phil's Trailhead
Phil Meglasson rides at Phil’s Trailhead | Photo by Cody Rheault

The Outdoors

Better known as one of sport climbing’s OGs, Kent Benesch dabbled in MTBs, eventually spending long days moving dirt west of Bend. His eponymous trail, along with Phil’s, finally gave riders the option of a mostly singletrack loop.

Ben Husaby didn’t even own a mountain bike in 1994, but the brawny two-time Olympic Nordic skier wanted new terrain for dry-land training. Pitchfork in hand, he began work on Ben’s trail adjacent to Skyliners Road shortly after Kent’s was done. Ironically, what he intended as a downhill trail would later become the network’s first one-way ascent. The sport of mountain biking was growing fast; people were filtering in from all manner of athletic backgrounds.

Phil's Trailhead sign
Photo by Cody Rheault

The Founders

In 1992, Central Oregon Trail Alliance (COTA) was founded in an effort to legitimize trail work. But after a few years, COTA’s relationship with the Forest Service (USFS) became strained as trails continued to proliferate under the tongue-in-cheek name early builders gave themselves—SORTA, the Society Of Rebel Trail Alliance. Frustrated by the USFS’ reluctance to acknowledge the value of more trails, the SORTA crew continued to dig, and Thomasberg challenged the USFS to “pay somebody to sit there and count cars with bikes on them.” The two groups counted together, and within weeks of seeing the large size of the MTB user group, the USFS was asking how it could help in a watershed moment. It went on to grandfather in much of the existing renegade singletrack it had earlier condemned.

The Black Rock Riders (shown) led by Phil, Bob Woodward and Dennis Heater (center, with a bike overhead).
The FRIENDS: In the ’80s, there were boomboxes, big hair and music videos on MTV. And there was the crew that helped not only build, but ride, the trails that would become Phil’s. Builders cleared the way for informal crews such as the Black Rock Riders (shown) led by Phil, Bob Woodward and Dennis Heater (center, with a bike overhead). While the Sony Walkman may have given way to Bluetooth, Phil’s Trail complex rocks on as an icon in the mountain biking world.

The Encryptors

Prior to this sea change, cagey builders wanted to distance themselves from their SORTA (il)legal work, so the trails were often given code names. Eric Vickers built the now garden gnome-lined E.L.V. trail, while Cody Davis toiled on the adjacent C.O.D.. Fortuitously initialed, Michael Thomas Beall built M.T.B. trail on the other side of the system. They may have been great trail builders, but master encryptors, not so much.

Like Phil’s Trail, C.O.D was at one time several distinct trails that were condensed for mapping purposes. One day, while Jimmy Terhaar and Kent Howes were digging on middle C.O.D., Bob Woodward happened upon them and discovered the trail. He griped about the upper part being a little boring. “You should call this one Y.A.W.N.” he went on to say. “I think we should call it Woody’s,” was Howes’ sarcastic retort. And Woody’s it was for several years.

Lev Stryker gets air at The Lair.
Lev Stryker gets air at The Lair | Photo by Katie Sox

The Loners

“Whoops” is a perfect colloquialism for a rolling ribbon of trail, but it was originally named “Frizzell-Frazzell” after its creator, Jeff Frizzell. Finding creative routes was nothing new to Frizzell, a world-class rock climber credited with a variety of first ascents at Smith Rock. High-schooler Bryan Harris helped Frizzell with Whoops, and other parts of Frizzell’s “Mt. Bachelor to Town” singletrack project that included significant portions of Flagline Trail. “I was making trail rakes in metal shop at school,” said Harris. “But, we didn’t know that [the trails themselves] existed.” Frizzell and Harris knew other trails were being created nearby, but builders were all working independently of each other. Now, nearly 30 years later, Whoops gets more use than any trail in Oregon, while Flagline, a late-summer classic, connects Bachelor to Bend via 100% singletrack.

Surprisingly, most of these characters are still in Bend. Or perhaps it isn’t a surprise at all. This kind of work breeds community. These guys may have just wanted new trails to ride, but what they created was something more – more meaningful for them and more impactful for the MTB community than anyone could have imagined. It’s hard to leave something like that behind.

A Trail by Any Other Name Would Ride as Sweet:

map of Phil's Trail System
Illustration by Mona Daly based on map provided by BendTrails.org

Storm King: Layton White built and named this one in honor of nine Prineville Hotshots who died in Colorado’s 1994 South Canyon “Storm King” fire. 

Marvin’s Garden: Named for Marv Lange, a former USFS employee who is credited by many for making Phil’s Trail network possible.

Tyler’s Traverse & Larsen’s Trail: Helping hands imparted trails with “more meaning that people know,” Paul Thomasberg said. These two trails invoke spirits of Tyler and Steve to remember their adventurous souls.

Mrazek: Phil’s ode to a quirky Czech-made bike that gained brief popularity in the ’90s.

K.G.B.: Kent Howes built “Kent’s Get Back” (or “Killer Green Bud” if you’re a horticulturist) to get home through what is now Tetherow.

Middle C.O.D/née C.I.A.: Builder Jimmy Terhaar originally named the trail “Cyclists In Action” only because the acronym was a fitting foil to K.G.B. While C.O.D. officially gets punctuation, it’s actually named for Cody Davis.

Grand Slam: Built by skier Scott Schauer, the original name, “Golden Schauer,” didn’t make it onto the official USFS map.

Hear more stories from Phil and friends on The Circling Podcast. | Read more cycling stories with us here

A Complete Guide To Mountain Biking in Bend, Oregon

Although the end of summer brings shorter days, fall weather brings phenomenal trail conditions for mountain biking in Bend, Oregon. Dry, dusty trails have been hit with some rainfall and cooler temperatures, creating that “hero dirt” mountain bikers are looking for.

In Bend, we are incredibly fortunate to have access to hundreds of miles of singletrack just minutes from our doorsteps. The trails range from family-friendly greens snaking through Ponderosa forests to black diamond jump lines and everything in between. We even have a bike park up at Mt. Bachelor. In Bend, there is a trail for every rider. Probably a beer, too.

Phil's Trail in Bend Oregon
Phil’s Trail | Photo by Samantha Weald

The Phil’s Trail and Wanoga Trail Complexes

With nearly 100 trails in the Phil’s Trail Complex, we’ll only touch on a few. Phil’s has something for every rider and every riding style. On the south side of the highway is the Wanoga Trail Complex. The area has 30 trails, and the riding is more advanced.

These are all multi-use trails, meaning you could encounter runners, hikers, and equestrians. Follow trail etiquette, which means yielding to other users. And be careful when descending. Some trails are directional, but others can be ridden in either direction.

It may be a small slice of the MTB pie, but these are some of the best mountain biking trails in Bend.

Two mountain bikers on Phils Trail in Bend Oregon
Phil’s Trail | Photo courtesy of Pine Mountain Sports

Beginner: Green Trails

When discussing mountain biking in Bend, it is hard not to mention perhaps the most well-known trail, Phil’s Trail. This beginner-level, or green, trail descends 684 feet over nearly 6 miles. If you ride Phil’s Trail, be sure to stop at the flaming chicken—you’ll know when you see it.

But, the Phil’s Complex has much more to offer. Linking the three Ticket to Ride trails together forms a nearly 6-mile loop. Rocky climbs, and long, fast descents push the green trail boundary. You can expect climbing and descending to be around 500 feet. Tackle this loop on any mountain bike and ride in either direction.

Phil’s and Ticket to Ride are both great options for kids. Ticket to Ride is especially ideal for kids who are ready for a bit rougher terrain. 

Intermediate: Blue Trails

Upper and Lower Whoops in the Phil’s Complex are excellent trails to advance your riding to the intermediate level. Upper Whoops is fast and flowy. While the trail has nothing overtly technical, it has excellent corners, allowing for easily maintained speed. But be aware of uphill traffic. Some riders like climbing Upper Whoops rather than taking the fire road. 

Lower Whoops, which is descending only, maintains the fast and flowy feel with the addition of more technical features. We’re talking jumps. The jumps aren’t mandatory, meaning they can be rolled or have a go-around. They aren’t small jumps, though. Ride carefully, even if rolling them. All of this culminates into a trail that is perfect for progression. 

You can expect to climb and descend more than 1,100 feet if riding both trails and pedal about 8 miles—4 miles up, 4 miles down.

Group of mountain bikers riding Tiddlywinks Trail in Bend
Tiddlywinks, Phil’s Trail | Photo by Max Rhulen

If you like Lower Whoops, Tiddlywinks is up your alley. Tiddleywinks sits in the Wanoga complex and takes Whoops to the next level with its length, tech, and speed. And jumps, lots of jumps.

Tiddlywinks offers riders a longer and faster ride through the forest. With its mix of rollable jumps, side options, and rock tech, it is an excellent trail for progressing as an all-around rider. Tiddlywinks is also a descending-only trail—no need to worry about riders coming up.

One of the most consequential features is an up-and-over rock roll about halfway down the trail. Look before you leap on this mandatory feature. Going over the bars isn’t out of the question, so don’t be too proud to walk.

Tiddlywinks Trail Bend Oregon
Tiddlywinks Trail | Photo by Max Rhulen

Advanced: Black Trails

Looking for an advanced jump trail? Look no further than Wanoga’s Lone Wolf. Lone Wolf starts with a technical rock roll into a short, technical descent. Squeezing between rocks and a tree, Lone Wolf then sends you into a 5-6 foot drop. If you find this to be too challenging for you, Lone Wolf may not be your trail.

Jumps of all sorts continue down Lone Wolf’s 1.5  miles. Expect mandatory doubles, hips, and step-downs averaging 15 feet as you descend nearly 500 feet. Again, if you are not a confident jumper, Lone Wolf may not be the trail for you. Fortunately, Lone Wolf is a descending-only trail—no thinking about mountain bikers climbing.

If jumps aren’t your thing, but you are looking for an advanced trail, head back to the Phil’s Complex and check out South Fork. Getting there is a bit of a bear, but fantastic views await you on the climb. With more than 3 miles and nearly 1,000 feet descending, South Fork always provides miles of smiles. 

South Fork is Bend’s option for fast, backcountry descents. The rough and rowdy track quickly gathers speed and incorporates roots, rocks, and natural corners. A modern, full-suspension trail or enduro bike is recommended. Although most riders descend South Fork, some do come up. Hikers, too, so be on the lookout. 

Phils Trail
Phil’s Trail | Photo courtesy of Cogwild

Other Options to Ride

With hundreds of miles of trails, we are just scratching the surface. Remember that mountain biking in Bend, Oregon, doesn’t stop when the snow flies.

Cline Butte and the Maston Trail System, just north of Bend, are great winter riding options. Maston consists of cross-country green trails with a few blues mixed in. This system is perfect for the whole family. Cline, just across the street, takes it up a notch.

The trails descending the butte are advanced. The terrain is very rocky, steep, and technical—only recommended for more advanced riders.

On the south side of Bend, Horse Butte is another excellent option in winter. These trails are great for the whole family, but it is important to note that the loops are rather long here. Most are more than 20 miles, with the shortest being 10 miles. But, as the trails are multidirectional, you can always ride in a few miles, turn around, and ride out.

Grit Clinics Bend Oregon
Grit Clinics | Photo by Katie Sox Photography

Food, Beer, Rentals, and Extras

No bike? Dying to try a full suspension? Bend has fantastic bike shops to rent from. Project Bike and Pine Mountain Sports offer top-of-the-line rentals.

When your ride ends, head to one of Bend’s many food cart pods. The Lot and On Tap have a vast selection of beer and food options that will make everyone happy.

Mountain biking in Bend is an excellent way to connect with others. Pine Mountain Sports has group rides on the first and third Wednesdays of each month. On the second and fourth Wednesdays, it’s ladies only. 

If Wednesdays don’t work, check in with other bike shops—Bend has plenty. If you want to ride solo, plan your route ahead of time. Bend Trails is a comprehensive resource, and having an app like Trailforks downloaded on your phone never hurts. Ride safe!

If you are looking for cold weather mountain biking information, click here. Read more BIKING articles with us here.

 

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