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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

Gravel Trails Lead Back to Cyclocross

Every Thursday evening, a race course is set on the grounds of  The Athletic Club of Bend. Tires are squeezed by thumbs to check air pressure, riders line up and a starting whistle blows. There are battles among friends and between strangers. Crashes happen. The beer tent erupts in cheers. Somebody wins. Six-packs of IPA are handed out as prizes. High fives are slapped. Then the course markings are gone before the dust even settles. Each September, the Thrilla Cyclocross Series has been the heart of casual bike racing here in Bend for 20 years.

Deschutes Brewery fields one of the largest teams at the local events. Some of their racers are serious athletes. Some are serious beer experts. Some aren’t serious at all—and that’s the point. Their spirit is core to local ‘cross, where it’s more about community than about rankings. Sure, some come to win. But more show up for sunset beers in a makeshift beer garden, to reconnect with dusty-faced friends at the close of a too-busy summer. Here, the efforts of racing are like dues to a social club.

Cyclocross is as fun as ever, but field numbers in America aren’t what they used to be. Portland’s Cross Crusade, the largest CX series in the world in terms of participation, has seen numbers decline from the 1,400-rider start lists at their peak to about half of that during the past several years. There are half as many UCI (Union Cycliste Internationale) level races in the United States today as there were five years ago.

Cyclocross
Oscar Guevara (left) and Jeremy Gomez (right)

What happened to the juggernaut that was American Cyclocross?

In a word, gravel. Gravel is—to borrow a refrain from Zoolander’s Mugatu—”so hot right now.” 

And there are plenty of reasons why: once quiet road rides feel choked with distracted drivers, and vast improvements in gravel equipment have made soft-roading easier than ever. Not to mention the collective aging-out of a generation of mountain bike riders who are losing their desire to “get gnarly” and finding a desire to just “get out there.” Of course, the global pandemic didn’t hurt the gravel movement either. With moratoriums on events and a sudden aversion to groups, we had more need than ever to escape the crowd, and gravel helped satisfy that urge for many. The wide open spaces of America—and of Central Oregon, in particular—had never been so attractive as from a bicycle during COVID. 

When the worst of the pandemic was over, and bicycle racing began to reappear, racers were eager to return to competition but had only been doing long, solitary days in the saddle. Gravel races—generally long, scenic, soft-road affairs—quickly assumed the mantle of “new normal” competition for many. And the more epic (read: longer) they were, the hungrier racers were for them. A 205-mile gravel race in Kansas, Unbound Gravel, quickly rose to become the most important bicycle race in America today.

Gravel racing is awesome. (Read more about some gravel biking routes in Central Oregon.) It’s hard to deny the beauty in covering 50 to 100 miles of new terrain in a day, especially with the help of a pack of riders chasing a finish line. But does it have to be so damn long? At what point does more become less? Finishing a monument like Unbound Gravel, at 205 miles (the mid-length course, mind you) may be the ultimate challenge for some. But what happens next? Ride the 350-mile Unbound XL? When is enough, enough?

Marcel Russenburger
Marcel Russenburger, 1981

Marcel

Everybody knows his name.

A soft haze of late September dust lingers at a rutted corner in the farthest reaches of a cyclocross track. With half of the hour-long race over, the gaps between riders are largely established, but Marcel Russenburger stands alone here, barking encouragement to riders in his Swiss-German accent nevertheless. Pinot, his half-wild, blue-and-brown-eyed dog pulls unrelentingly at a too-long leash. Sixty-four years old, Marcel wears the clothes of a carpenter just done with a project, a few specs of sawdust in his bushy gray hair. Complementing his well-used denim work pants might be a purple fleece vest from some race he won in 1990. Because before he was a carpenter and a father and a spectator, he was a Cyclocross star. A man who finished fifth at the 1985 CX World Championships, representing Switzerland.  

“Go Kalle, you can get him!” he shouts, emphatically. I doubt he is right, but I momentarily try harder. The least I can do is try a little harder. A few moments later I’ll hear a similar spur from Marcel to the rider chasing me. I might be one of his favorites, but he has a lot of favorites. His daughter, Sophie, is near the front of the women’s race tonight, but Marcel would have shown up to walk his dog and watch the races unfold regardless. Everybody knows Marcel. We are his people. And he is ours.

It’s time for a return to Cyclocross.

Where winning is winning, but losing might also be winning. Where ephemeral courses crop up in a park, or a pocket of fallow land around town. Where there are no personal bests, or course records, no awards ceremonies to wait for. Just people trying hard or not very hard at all on their bicycles for a little while. Trying in hopes of being first, or being proudly last, or just being better at something that’s difficult.

Several categories on course all at once ensure that casual spectators can’t really tell who’s winning or losing. That you’ve been lapped by the leaders (okay, twice) might hurt your ego at first, but nobody notices or cares. The crowd is enthusiastic and vocal, encouraging riders with light hearted heckling. Many of the spectators were racing an hour or two ago, and after a post-race recovery beer, they’re full of advice—good or bad. And they’re eager to share it.

A ‘cross race is the least intimidating introduction to bike racing there is. Aside from foot-tall wooden planks across the track, barriers to entry are few. Anybody over age 12 can compete at the Thrillas, and any bicycle will suffice. The races are short, and there’s no risk of getting lost or dying of exposure. You don’t have to be a nervous parent or a first-timer to appreciate these conveniences. Even as a pro, I’ve enjoyed spectating the final laps of races I’ve started—when equipment fails or the legs say, “maybe next week.” It’s a far cry from other disciplines that can leave you isolated for hours, riding for survival.

‘Cross is as shiny and relevant and authentic as ever. With the awkward return from COVID behind us, and diminishing returns from over-long gravel races looming, let’s look forward to what could be a Renaissance of cyclocross in coming years. If you like bikes or beer or people, maybe you’ll even decide to join the ranks. Your old gravel bike would work just fine.


Read more BIKING in Central Oregon with us.

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