"Hippies built that," Timmy says as we pedal past a crumbling stone kiln on the edge of the road, his full-face helmet resting on top of his head. It's a large limestone oven, roughly the size of a small trailer, built into the side of a hill. It looks historic, like it should have a plaque commemorating its construction. "We got a hippie problem in Helena."

He's kidding. Helena, Montana, is a working-class town of 30,000 filled with people who hold state and federal jobs. Timmy is the closest thing Helena has to a hippie, with his shoulder-length blonde hair and endless stories about Burning Man. He showed up 15 minutes late for our group ride this afternoon, apologizing because he had to blow dry his hair.

Local Brian Elliott field tests potential routes for the enduro series, which he organizes.

I'm pedaling slow and steady up a one-lane road with a group of Helena's core riders—Emmett Purcell, Taylor Anderson and Timmy Wiseman—the guys who put sweat equity into the town's South Hills trail system, an 80-mile network of singletrack coursing through the foothills on the edge of town. South Hills is a mix of city park and Forest Service land, comprised mostly of sloping meadows, tall pine trees and narrow canyons with Wild West sounding names like Grizzly Gulch.

Purcell, one of the longtime visionaries of the system, leads us off the paved road and starts pedaling up a dusty trail that traces the seam of one of the forest's narrow, dry creek beds. Soon, the climb moves from slow and steady to steep and relentless. The slopes rising from the ravine are covered in a tall, gray grass with hundreds of dead lodgepole pines scattered across the ground like massive pickup sticks—the work of an invasive beetle that's systematically eating its way through the forests of Montana. The ravine we're pedaling is called Dump Gulch; miners used to come up here to ditch their trash. You can still find broken glass mixed in with the crushed-limestone dirt. Dump Gulch is one of the classic bike routes into the South Hills trail system, leading to long ridgeline trails with epic views, rocky domes and fast descents. It's a good, worthwhile climb, but a lot of mountain bikers don't bother with it anymore. Why pedal up a gulch when you could just catch a shuttle?

Emmett Purcell leads Timmy Wiseman and the author on a classic Helena ride in the South Hills trail system.

Dancing on acid

Helena, a gold-mining boomtown that found staying power as the state capital, has a lot of charming qualities, but it doesn't have the cachet of Bozeman or Missoula. It's not a college town. It's not a ski town. It's not on those "10 Coolest Cities" lists. It's a working-class town where people have 9 to 5s. But if singletrack is like gold (and let's be honest, singletrack is like gold), then Helena is experiencing its second boom as Purcell and his cohorts unearth former miner trails and motorcycle paths, clear deadfall and scrape away the top layer of scruff. They're like archaeologists, uncovering and enhancing a massive system with more than 20 access points scattered throughout town. In the process, the city of Helena has embraced the mountain bike, adopting the unofficial motto, "Every street ends in singletrack."

Chase Peaslee, Wiseman and Taylor Anderson take the Bike Helena shuttle bus.

Even better, the city started a shuttle called the Trail Rider that whisks riders from town into South Hills, hitting a different trailhead five days a week during the summer. And it's free.

Helena's love affair with dirt started 18 years ago when the city passed a $20 million bond to protect the South Hills system. Then, in 2013, it used a new hotel bed tax to fund the Prickly Pear Land Trust's preservation and trail maintenance efforts and created the Trail Rider.

"How do we take Helena to the next level? That's what we were trying to do," says Pat Doyle, the former city tourism official who helped develop the idea of a free shuttle. "We wanted to create something that was sustainable, and the trails infrastructure was already in place. A lot of cities in Montana have access to good singletrack, but few of them are promoting it."

Since its launch, the Trail Rider has expanded from running on Saturday mornings to running five days a week during the summer. "People love it," Doyle says. "We have businesses asking to participate in the tax because they see the value that the trails and shuttle bring to the community."

Wiseman, Anderson, Elliott and Purcell look over the town of Helena.

The Trail Rider has turned what was traditionally a cross-country system that demanded a long climb from town into a series of fun, almost effortless descents, most of which end at a brewery. It's difficult to reconcile Helena's fun-loving, low-effort style of mountain biking with Montana's scrappy, frontiersmen character. Plus, I'm a firm believer in suffering. Maybe it's my Catholic upbringing, but I don't believe you're allowed to have fun until you've put in some solid work. I've come to Helena to work through some of my hang-ups and see if I can learn to love the shuttle.

Ironically, though, we opted to pedal today, climbing 1,600 feet from the center of town to the summit of Mount Helena. At the top, we leaned against our bikes to survey the city below. A tall, European-looking, gothic cathedral stands in the center of town surrounded by storybook neighborhoods. You can see the gulches taking shape just outside of downtown, running like fingers into the various ridges on the horizon. They have been the highways into the mountains for more than a century, first for miners who came here seeking gold, and now for the mountain bikers who mine the area for perfect dirt.

The trees that line the edge of the rocky knob are short and gnarly, with pine needles sprouting from the ends of branches in tufts. The trail drops immediately from the peak over sharp, jagged rocks, forcing you to pick your line through awkward rock wedges and fins before you hit a course of quick, half switchbacks inside a rutted-out goat path with knee-high rock drops. Wiseman rides it fast and loose, slapping his back tire through the corners. We hang a right on Hogback, which has some imposing chunky sections with a boulder kicker that launches you through a rocky notch with a blind landing. I walk it, but the locals send it with alarming speed. Anderson, a father of two who skipped work to ride with us, hops through most of the chunky rock, his bike in the air as much as it's on the ground.

"Hogback sucks me in every time," Wiseman says, pulling off his helmet and running his fingers through his hair. He and Anderson run laps on the rocky notch, dialing it in while the rest of us watch. "It's like dancing on acid. You think you can quit anytime, but you just keep dancing."

We pick up Ridgeline—an appropriately named trail that Anderson and Purcell have been riding for at least two decades—as it contours along a small grassy hump with a view of the Sleeping Giant, a series of mountains that resembles the profile of a man taking a nap. Ridgeline moves between meadows and patches of lodgepole pines until it hits Show Me The Horse, a skinny piece of brown dirt cutting through yellow grass with pines rising on the hump behind it, like a patch of hair. It's incredibly fast, with low berms cut into the corners and the occasional small kicker. I count exactly three rocks on the entire trail. The dirt is super tacky thanks to a quick rain earlier in the day, allowing you to lay into the corners. As long as you can hold on and keep the front tire pointed in the right direction, you can carry all kinds of speed.

South Hills has a western quality to it, full of open meadows with long-range views, like we're going to stumble across a cattle drive at any moment. The riding is full throttle, with long sightlines, few blind corners and trails so buff I find myself pushing my bike faster and faster. The whole system seems to be built for speed.

"But when something goes wrong, it's a trip to the hospital," Anderson says.

When I tell the guys how beautiful I think the riding is, they seem surprised, and quickly change the subject to another trail system in another town that's blowing their minds right now.

"That's just Helena," Purcell tells me later, when I ask why his buddies seem to eschew any compliments. "We're not scared to be humble."

Purcell and Peaslee ride off the daily grind on a foggy Helena evening.

Through the Notch

Purcell and I are working our way up a perfect bench-cut, which rises through an understory of skinny bushes whose silver-dollar leaves form a golden tunnel as they turn yellow with the season, when he tells me about his competitive unicycling career.

He spent years developing his one-wheel skills around town, doing trials-like drills on the low walls that line some of the parks. He participated in the Unicycle World Championships, and even performed at a half-time show at an NHL game. Purcell is the kind of guy who turns hobbies into obsessions. These days, it's yoga. He tells me about these torture-like postures he does in which he uses added weight to force certain muscles into deep stretches. It sounds horrible, but he's 50 and can slay most people half his age, so I'm thinking about getting into yoga too.

We're on the Hanging Valley trail, a backcountry gem about an hour outside of Helena that rarely sees tires because the singletrack around town is so damn convenient. There are half a dozen big backcountry trails like this within an hour of the city, including a ripping descent from the Continental Divide that the Trail Rider shuttle hits during the summer. Hanging Valley is a lesser-known out-and-back that demands lungs and legs on the initial ascent. There's no shuttle here.

Purcell navigates the steep, rugged terrain of the Hanging Valley trail, a rarely ridden gem located in Helena’s backcountry.

We gain 2,000 feet over a few miles, with Purcell doing the occasional spat of trail maintenance along the way. The thick ground cover, which was green near the trailhead, shifts to bright pink as we get closer to the top of the mountain. It looks like someone spilled paint.

Hanging Valley couldn't be more different than South Hills. If South Hills is arid, almost desert-like, then Hanging Valley is damp and cloudy. If South Hills' trails are buff with hero dirt, then Hanging Valley is littered with roots and loose shale. It's slippery and messy. Rugged and adventurous. There's no brewery at the bottom of this trail. Just a campground with a couple of pickup trucks.

A bright green moss pops off the Douglas firs and a white mist fills the spaces between trees as we hit the peak of our climb. It's moody as hell. I put on all my layers to fight the damp chill before we drop elevation via a dozen fast switchbacks into a narrow valley flanked by steep slopes. Eventually, the trail bottoms out between tall limestone cliffs, which continue to narrow until you're staring into a notch where the trail drops steeply through the heart of the cliff system. The gap is just a few feet wide, with white, limestone walls rising 100 feet on each side. The trail is riddled with broken rock and drops steeply, demanding you huck off a boulder and immediately pin a dogleg to the right under a small arch.

I stash my bike and climb down the nastiest patch of trail, but Purcell gives it a go, riding his brakes and surfing, tires locked, on the loose rock. After the arch, the trail opens up and mellows out, but it's covered in several inches of loose rock so it's like riding on marbles. The limestone cliffs rise even higher, their white walls punctuated by little green plants that look like cilantro growing out of nooks. The trail ends on the edge of the cliff, overlooking the belly of Trout Creek Canyon, which is reminiscent of the Italian Dolomites with its dramatic rock spires and fins.

We drove an hour into the mountains and rode for two hours to reach this point on the edge of the canyon. We have a long push back up the way we came and then a long and fast downhill back to the car ahead of us. It took a lot of effort to stand on the edge of this cliff and look into the heart of Trout Creek Canyon. And this is just the beginning of our day. Purcell looks at his watch. "We should get moving if we want to catch the shuttle back in town."

Wiseman isn’t deterred by a few chunky rocks.

Here We Are Now, Entertain Us  

All anyone can talk about on the shuttle is the quality of dirt. It's been raining off and on for a few days, so everyone's geeking out about the "moisture levels" as the bus takes us through a neighborhood with ranch houses where people are raking leaves and cooking on grills. The shuttle is big, like a bus you'd see on a college campus, with room for maybe 25 riders inside and a trailer with space for just as many bikes. A few hikers sit up front and our crew has added Brian Elliott, a former moto racer who organizes the local enduro series.

Anderson, who has two young children just beginning to rip, tells me the shuttle has been huge for his family. "It cuts out what would be an hour-long climb for my kids and opens up South Hills."

It feels a bit like cheating when the bus drops us off at the trailhead for Arrowroot, which consists of a small climb before transitioning into a flowy downhill with long-range views over a high-grass meadow. I'm used to suffering for my downhills. Even the downhills on my home trails have significant uphill portions. But if Helena has a signature kind of ride, it's this: a skinny line of chocolate-colored dirt winding through a meadow of tall grass. Big views. No rocks, no roots. Just fun.

Screw my work ethic; I kind of dig it.


We hit Entertainment, which is packed with high-speed rollers through an open pine forest, playing out like a slalom course through the trees. The joy comes from carving deep into the soft turns and trying to carry speed through the transitions. Entertainment is the first trail that Purcell and Anderson started cleaning and reworking decades ago, when Purcell was racing and Anderson was in high school. It's an old moto path that they spent countless afternoons rehabbing: cutting logs, rerouting fall-line sections and digging water breaks.

At the bottom of Entertainment, there's a small jump park that the locals have been working on, but it's Montana, so there's also an archery range right next door. I like the symmetry. Elliott and Chase Peaslee bang out a couple of laps on the jump line, but we decide to book it back into town to catch the second shuttle. This is the beauty of Helena's Trail Rider. You time it right and you can run two or three laps, getting thousands of feet of vertical drop and only pedaling a little bit uphill. It's the basis of the entire lift-served industry. People pay a lot of money for this kind of riding, and Helena is giving it away.

By most accounts, mountain biking is a pain in the ass. You have to load your bike in a truck and drive an hour or so into the mountains and then you spend most of your time suffering up one side of a mountain just for a few minutes of bliss coming down the other side of a mountain. And I'm okay with that. Mountain biking is fair. Your reward is dictated by the amount of effort you put into it.

But here in Helena, it's all reward and very little effort. The trails are right out your door. There's a free ride up the mountain. It's effortless. It's all entertainment.

Bikes stored inside the Blackfoot River Brewing Company.

Singletrack to Beer

Even the kids are badasses in Montana. We pick up a family of rippers on the second shuttle, the dad rallying everyone in his household as soon as he heard the Trail Rider was running. The 13-year-old daughter and 10-year-old son left their homework half done on the dining room table.

The shuttle drops us off at a different trailhead and the climb is a little more stout, following a long sidecut through a broad, open slope that rises a few hundred feet. I can feel Eva, the 13-year-old, breathing down my neck on the climb, so I pull over under the pretense of taking a picture but really, I'm just letting her pass me before she has the chance to say, "on your left."

There's a thick fog at the top of the climb, so when we pull off the main trail to follow a faint path cutting through the grass, it looks like we're going to pedal off the edge of the mountain. By the time I reach the group at the edge of the ridge, they're deep into a conversation about Keanu Reeves' gun skills. Elliott's talking about a video where the actor works his way through a shooting course with a 9 millimeter.

"Google it," he tells me. "It's insane."

Then Wiseman points to a small cabin on a distant peak on the horizon and tells me the story of the guy who built that cabin with his own two hands. While living in a teepee. I'm starting to get the feeling that everyone in Montana is way tougher than I am.


We're on Top of the World, which starts wide open on a small, rocky dome with a little drop as the ridgeline trail moves from rock to dirt, then it hits a sharp left before dropping into the trees and connecting with Rent Money, which is Wiseman's personal passion project. It's also the first mountain bike-inspired trail the locals have built, full of big, sweeping turns that challenge you to go higher and faster through the berms, and big rollers that take your breath away like a roller coaster. We hug a sidehill with a massive open meadow via bench-cut dirt as the clouds move in over the dark green mountains behind us. The flow is addictive as the trail weaves through lodgepoles and brush piles stacked by the Forest Service, waiting to be burned. Then it gets pumptracky with quick, serpentine turns separated by rollers. The dirt is grabby, like Velcro. I get why the locals are so stoked. I'm not used to trails that are this smooth.

"Oh yeah," Elliott says. "The only roots out here are in Timmy's hair."

All the trails seem to funnel back to the city. It's getting dark, so we link some dusty singletrack that takes us through a series of bench cuts hanging on the side of the slope above the city. We pedal across a number of ravines, each with a water line that serves Helena, and pedal along the edge of a white, crumbly cliff before topping out on a dome that stands tall above the edge of downtown. There's some graffiti on the rock and a chain-link fence in the corner. Anderson points out the trail we'll take from the dome into one of downtown's main streets—it's tight and drops fast off the side of the hill before hitting the pavement. Blackfoot River Brewing is maybe three blocks away.

"Singletrack to beer," he says. "That's as good as it gets."

Purcell rides his backyard pumptrack with Keenan Charlton.

Circle of Death 

The pumptrack has taken over Purcell's backyard. It's an incredibly elaborate system of rollers, tabletops and huge berms with an oval track in the center affectionately known as 'The Circle of Death.' Christmas lights are strung through the trees so he can ride it at night. Purcell lives in a nice, two-story brick home on the edge of downtown. Wiseman lives in a tool shack in the backyard and Anderson and his family live next door. They call it the '800 Block Bike Commune.' After a few post-ride beers at Blackfoot, we decided a pumptrack session under the lights was in order.

Mountain bikers come and go, toting six packs and taking turns riding under the lights. The star of the show is a teenager named Keenan, who starts doubling rollers until he gains enough speed to gap into the Circle of Death. He has his own lines through the track that no one else can follow.

"I'm about to have a Tonya Harding moment," Wiseman jokes, watching the kid stomp the dirt.

The cathedral bells ring at 9 p.m. We talk about trying to sneak another ride in in the morning, but Elliott says he can't make it because his wife is making him go hunting. "You'd be shocked at the amount of elk meat I have in my freezer," he tells me. Later I learn that Brian's family used to have 4,000 acres in the mountains near Hanging Valley, but his great, great grandma lost the property in a poker game. Because this is Montana, and that's what grandmas do.

When it starts to rain, we cut the pumptrack session short and consider pedaling to another brewery. I'm tired and think about calling it a night, but Anderson convinces me to stay the course. "Don't worry; it's pretty much all downhill to the brewery."

Of course it is. Because this is Helena. Everything's downhill.

Want to visit? Find all the information here.