Four laps into my first-ever cyclocross race, I’m feeling better than expected; 35 minutes of balls-to-the-wall racing, and I’m hanging on in the top half of the 86-man field. Never mind that it’s the beginner field, or that I’m the only one benefiting from a high-performance titanium bike. I’m just relieved the unicyclists haven’t caught me and, more surprising, that I’ve managed to stay on my bike.

“Last lap!” calls out a stranger. “Leave it all out there!” As I’ve already left a flat tire and any real chance of winning behind me on the course, this tossed-off encouragement sounds like a reasonable strategy, so I go for it. Sprinting across the rolling terrain, I reach the twisting, spectator-friendly “Pain Cave,” where the course funnels into a series of steep, mud-slicked hills that culminate in a 40-degree heartbreaker.

The Fittest and Fattest Cities: Reader Poll>>> 

Most other mid-packers are simply walking their bikes up at this late stage, but I stand up in my pedals, inspired by the stranger’s words. The beer-soaked, cowbell-clanking crowd responds, cheering loudly as I grind my way up the slope, back wheel fishtailing wildly. One stroke from the crest, I lose all traction, my foot touches down, and, without missing a beat, the cheers turn to good-natured heckling (“Nice try—too bad it’s your last chance!”).

Welcome to Portland, OR, America’s Fittest City.

Cue the eye-rolling. We know what you’re thinking: Not another paean to the caffeinated, fixie-riding, beer-quaffing, rain-soaked vegan hipsters of Portlandia fame. Or maybe you’re calling for a recount that’ll put body-obsessed Long Beach, CA (No. 12 Fittest), or trendy, park-heavy New York City (No. 19) at the top of the list. But what makes a city fit, anyway? It’s got to be about more than pumping iron and eating vegetables, or even spending time outdoors and staying active through winter? Surely socioeconomics and smart planning play a role. And what about good, old-fashioned positive attitude?

There are dozens of ways to measure “fitness”—our 15-point proprietary formula accounts for conventional fitness as well as air quality, pedestrian and bike friendliness, obesity rates, general wellbeing, and other factors—and, all things considered, the Rose City topped our Fittest Cities list fair and square…and for the second straight year, no less. Clearly, Portlanders are doing something right.

The 2014 Fittest and Fattest Cities in America: The List>>> 

To get a better handle on what Portland’s secret is, I spent a week trying to keep up with the citizens of the nation’s fittest city. Here’s what I discovered.

[pagebreak]

NO. 1: FITNESS NEEDS TO BE FUN

My first stop is Portland International Raceway (PIR), where the city’s famously fun and filthy Cross Crusade cyclocross series is hosting its seventh Sunday race of the season. The best kind of spectator sport, cyclocross pits cyclists against a short technical circuit that traverses grass, dirt, pavement, mud, and sadistic, Tough Mudder–inspired obstacles—sandpits, stairs, ditches, and barriers—at full speed. Mistakes are commonplace, and crashes de rigueur. Though it was born in the cold, muddy winters of early 1900s Europe, cyclocross is now the fastest-growing bike-racing competition in the U.S. 

That’s because, despite the inherent challenge, it’s fun as hell. “Cyclocross is a hard sport, but it’s relatively safe,” says race director Brad Ross. “If you fall over, chances are you’ll just get muddy. Then you’ll stand up and laugh about it.” Sure enough, I see dozens of racers hit the turf, but most are smiling so broadly there’s mud in their teeth.

The 2014 Fittest and Fattest Cities in America: 8 Interesting Facts from Around the Nation>>>  

The Cross Crusade is the most popular cyclocross series in the country, attracting 1,100 or more participants every fall weekend with its welcoming, family-friendly atmosphere and Portland-style lack of pretense. “It’s a competitive scene,” says Ross, “but we make it as easy and fun as possible for anybody and everybody. It doesn’t matter if you’re a man or woman, or how old you are, or what fitness level you’re at—you can come and race your bike.” The atmosphere at PIR is more music festival than exclusive, hardcore sporting event. Early on, the smoke of bonfires drifts across the course while food trucks and breweries set up shop for the day. Around midday, a drum corps performs while toddlers practice cornering and overcoming pint-size barriers in noncompetitive Kid’s Cross races.

All of it works to drive participation, something that’s important in a fit city. Alongside the typical racing set—grim, Lycra-clad men with sculpted, sinewy legs—are senior citizens, awkward adolescents, big-boned amateurs, hipsters in jean shorts riding anything on two wheels, and, improbably, those crazed unicyclists. They all compete hard and, at the end of the day, wear the same uniform—mud. Post-race, riders eat pork sandwiches and sip craft beer while socializing around bonfires or taunting their friends. It’s a rollicking good time and, after finishing 37th in my race, I join in the party.

Two days later, Just a 15-minute bike ride from the glass-and-concrete high-rises of downtown, I get my first taste of Portland’s urban wilderness in Forest Park. That’s where I join Dave and Paula Harkin for an afternoon run on the 30-mile-long Wildwood Trail, a classic route that hairpins and switchbacks across the ridges and ravines of the 5,000-acre park. The Harkins—co-owners of Portland Running Company—have general manager Zach Mione in tow; together, the three have the trim physiques and well-muscled legs of competitive runners. My legs, on the other hand, are feeling a tad wooden from Sunday’s off-road race.

The 2014 Fittest and Fattest Cities in America: The Runner-Ups>>> 

Soon, we’re running alongside Balch Creek, a burbling trout stream that winds beneath centuries-old Douglas firs. The forest is an absolute riot of green—moss drips from the trees and ferns sprout from every square inch—and I can’t believe we’re still in the city. This is one of the nation’s greatest urban forests (other top woodlands are in Seattle, Denver, Minneapolis, Austin, Charlotte, Milwaukee, New York, Sacramento, and Washington, D.C.), a place where elk graze on sword ferns and black bears are occasionally spotted. Portlanders hold the park dear, and flock to it for hiking, biking, and, of course, running.

But it’s more than just nature that energizes the local running scene. “Most of the longer-distance professional runners for Nike live and train in Portland,” Mione says, “so you’ll run along the waterfront and see [Olympians] Galen Rupp or Alan Webb or Kara Goucher.” Beyond the pro culture that Nike infuses, amateurs like the Harkins—both accomplished runners who organize races and have coached thousands of marathoners—get people involved through friendly track and cross-country races and regular group runs.

“I grew up in Seattle,” Dave says. “It’s a bigger city, but there’s so much less activity universally. Down here, it feels like everybody I meet has done a marathon or some kind of serious endurance event.” (In fact, Portland is the nation’s most active city, with 86% of the population getting regular exercise.) Over the next 2.5 miles, our run starts to feel like a serious endurance event—Paula, not feeling well, turns back—as the trail climbs 900 feet to Pittock Mansion, a city-owned landmark that looks out over downtown to the snow-covered Mount Hood.

10 Ways Yoga Benefits Endurance Training>>>

As he takes in the city, Dave tells me that Paula’s on a five-year streak of running every single day, and averaging something absurd like six miles per run. She’s a hard-charging competitor, in other words, but she doesn’t need to prove anything to us on this outing. Like her, Portland’s runners don’t take themselves too seriously, as evidenced by the sheer number of beer and pub social runs.

It may be a small thing, but having such an easygoing, anyone-can-do-it attitude may be one of the things that makes Portlanders so active and fit. It’s empowering, after all, to be able to say you’re an athlete and feel competitive yet not feel like crap because you’re not elite. Mione, an able runner who races casually, sums it up best: “I could run the best race of my life or the worst, and the result is I’m going to go have a meal and a beer, and feel pretty good about having run it.” As we head back down the trail, echoes of the cyclocross reverberating in my legs make the thought of a post-run burger and beer all the more appealing.

[pagebreak]

NO. 2: YOU GOTTA WORK OUT

Portlanders are famously outdoorsy, despite a decidedly damp climate that features 164 days of precipitation a year. “There’s no such thing as bad weather,” goes one variation of the local boast, “just bad rain gear.” But I’m not local, so on the morning of my Wildwood run—when it’s still gray and pissing down rain—I head indoors to sample the local gym culture at Firebrand Sports.

“I could bring LeBron James down like a baby,” brags Firebrand owner Sara Stimac, whose 10,000-square-foot fitness studio is part of a new crop of boutique gyms in the warehouse-rich Pearl District. Her threat sounds a touch hollow to me, especially considering that the “addictive, total-body, shirt-drenching, muscle-shaking” class I’ll be taking is Pilates-based.

The 14 Best Things You Can Do for Your Body>>>

But by 7:03 a.m.—exactly three minutes into Stimac’s 50-minute “Pyrolates” session—my legs are quivering like Jell-O. I’m perched on a Megaformer, a giant, tricked-out Pilates machine that looks sort of like a medieval torture device, performing painfully slow, controlled lunges that are working my muscles to failure with alarming efficiency. Right when I’m having my Bambi legs moment, Stimac, who’s been cheerily prancing around the studio making subtle form corrections, tells the class to “pulse.” The women respond by coolly lowering into a deep, sustained lunge, while a middle-aged guy cries out like a wounded animal. The sweat pours from my brow, but I manage to squeeze out a few pulses. Looking slightly amused, Stimac tosses me a towel.

8 Amazing Fat-Burning Intervals>>>

Unlike cities where “people think fitness is hard, it’s not fun, it’s drudgery,” Stimac tells me after class, Portlanders tend to incorporate it into their beloved outdoor activity, regardless of the miles they’re logging or the dismal weather; so there’s not a huge gym culture here, as there is in Long Beach, Oakland, or D.C. (which have as many as five times more health clubs per capita). Stimac discovered the Megaformer—an invention of Hollywood fitness guru Sebastien Lagree—in gym-crazy L.A., and is trying to persuade more locals to come indoors to exercise. As for me, I hobble out of there, confident that all too soon I’ll be regretting that I did.

[pagebreak]

NO. 3: NATURE IS YOUR FRIEND

It’s no wonder Portlanders love to get fit outdoors. Set at the confluence of the Willamette and Columbia Rivers and surrounded by mountain ranges and forests, the city is at the heart of a sprawling wilderness playground. In a 20-mile radius of downtown, 1,250 miles of bike and pedestrian trails traverse almost 40,000 acres of protected parklands. Within a 90-minute drive, Portlanders can choose from: hiking to a waterfall, riding epic singletrack, or windsurfing in the Columbia River Gorge; year-round skiing on 11,249-foot Mount Hood, whose snowy summit is visible all over town; whitewater rafting or kayaking on the roiling White Salmon, Klickitat, Wind, and Clackamas Rivers, all of which tumble down from the Cascades into the Columbia; surfing Pacific Ocean swells at Cannon Beach; and rock climbing at Broughton Bluff, or bouldering at Carver.

Slightly farther afield are Washington’s Olympic Mountains, Mount Rainier, and, to the southeast, the high desert of eastern Oregon. That’s where I head on Friday, eager to explore the Cascades’ rain shadow. 

The 5 Most Climbable Mountains in the U.S.>>>

Fewer than three hours from Portland and slightly north of the adventure mecca of Bend, OR, the 550-foot-tall tuff-and-basalt cliffs of Smith Rock ply the lava plains like a wayward ship. A world-famous sport-climbing destination, the rock formation is wrapped in a turn of the Crooked River and protected by a 651-acre state park that’s crisscrossed by a tangle of hiking trails.

Under a warm autumn sun, I spend four or five hours rambling over nearly half of them. From the summit, I spot Mount Hood and, to the west, the volcanic Three Sisters. Down beside the Crooked River, I’m treated to a show by a family of six river otters, which swim against the slow-moving current, fishing their way upstream. Far above me, miniature climbers scale the impossibly sheer crags and overhangs of the Dihedrals and Morning Glory Wall.

Heading out, I spook a concealed bobcat, and it explodes from its hiding spot and bounds off through an outcropping of trees and out of sight. Even though this popular park attracts half a million visitors a year, right now it feels untamed and remote. I can’t help but think that, if I lived in Portland, I, too, would be outside almost every day exploring the region’s natural beauty, weather be damned.

Adventure Running for Urbanites>>>

That soggy, mild weather seems to play an important role in the city’s fitness. Portland, for its rainy reputation, actually gets less precipitation than most East Coast cities. But it’s spread out into a lot of drizzly days, whereas New York (No. 19 overall) and Miami (No. 13) get isolated thunderstorms that can drop an inch or two at a time. As far as Portlanders are concerned, putting up with the mist is a small price to pay for snow-free winters and warm, dry, sun-splashed summers. It means they can bike and run and play outside year-round, and if the winter rains start bringing them down, they just strap on their skis up in the snowy Cascades.

And, like five more of our top-10 Fittest Cities—No. 2 San Francisco, No. 3 Seattle, No. 4 Denver, No. 8 San Diego, and No. 10 Oakland—Portland has a relatively mild climate where summers aren’t stiflingly hot or humid and winters feature little or no snow. It’s a recipe for year-round physical activity.

[pagebreak]

NO. 4: TWO-WHEEL IT AT EVERY OPPORTUNITY

In case you haven’t heard, Portland is a cycling paradise. With its purpose-built bike infrastructure, year-round mild temperatures, and relatively flat terrain (compared, say, with the thigh-burning hills of No. 2 San Francisco and No. 3 Seattle), more people get around here on two wheels than anywhere else in the country. I decide to join them when I arrive in town, and on Monday rent a road bike from Waterfront Bicycles, a friendly, no-frills shop in the Old Town District that boasts the city’s largest rental fleet.

Crossing eastbound over the Willamette River on the Hawthorne Bridge, I feel as if I’ve just merged onto a bike commuter superhighway (7.7% of men commute by bike here, nearly double runner-up Seattle).

America’s Best Bike-Commuting Cities>>>

It’s the evening rush hour, and cyclists are leaving downtown office jobs by the dozens, streaming across the traffic-choked span past a line of idling cars full of people trying to do the same. This bridge averages an astonishing 8,000-plus cyclist trips per day—and it’s only one of four downtown river crossings.

Once I’m on the road, it’s even clearer why so many people are out riding. The city practically trips over itself to accommodate bicycles, and it shows in the infrastructure. Cruising the Southeast District, I encounter signs every few blocks pointing the way—with distances and ride-time estimates—to nearby neighborhoods and major landmarks, making navigation intuitive. Bike lanes and boulevards extend in all directions, like red carpets inviting me to explore the city, safe from traffic.

Smartest Cities for Men>>>

In front of bars and coffee shops, bike corrals that accommodate a dozen bikes occupy what were once single-car street-parking spots. Green-painted “bike boxes” allow cyclists to wait ahead of cars at red lights, giving them a few feet advantage when the lights change. Even motorists seem genuinely concerned for my welfare.

I could get used to this, I think, and over the next few days I put in 80-plus miles just getting around and scoping out the city.

NO. 5: YOU HAVE TO PLAN AHEAD

Portland’s bike utopia didn’t develop by accident, or overnight. It’s the result of decades of smart planning by local government. In fact, the entire region, including three counties and 25 cities, has a single governmental agency, called Metro, that’s overseen urban growth since 1979, resulting in a built environment that, research consistently shows, encourages healthier lifestyles.

If you build it, says Jennifer Dill, Ph.D., director of Portland State University’s Oregon Transportation Research and Education Consortium, they will come. Bike parking, well-lit multi-use paths, integrated public transportation, and protected lanes all increase ridership. In fact, the number of cyclists locally has increased sixfold since Portland started earnestly growing its bike network 20 years ago.  The upshot is that it’s the only major city to have been granted platinum status by the League of American Bicyclists. 

The 10 Best Mountain Biking Trails in America>>>

Next on the docket for Portland? The latest land use plan calls for “20-minute neighborhoods”—that is, areas where residents can access restaurants, markets, schools, shops, and parks all within a one-mile (or 20-minute) walk from home. These walk- and bike-friendly areas should greatly reduce car trips. And the resulting public health impacts can’t be overstated, Dill says. In her opinion, creating an environment “where it’s easy, comfortable, safe, and enjoyable to walk and ride a bike for everyday transportation” is where American cities—particularly walk defiant Nashville, TN (No. 44 overall) and bike-hating Detroit (No. 47)—stand to make the biggest overall improvements in fitness and well-being.

If you want to see the long-term fitness benefits of regular cycling, look no further than the Portland Wheelmen Touring Club (PWTC), one of the area’s largest recreational cycling groups; but when I join them for a chilly, damp Wednesday-morning ride, they’re pared down to a group of 17, mostly retirees.

“We’re not exactly kids here,” says ride organizer Bud Rice, 69, a bulldog of a man with a paunch and thinning hair. “Our average age is 60, and most of us are retired.” That’s a relief, since my abs are cramping, my legs are weak, and, thanks to Firebrand, my ass feels like I’ve just come off the bull-riding circuit.

The Best No-Hassle Mountain Bike Getaways>>>

On their bikes, though, these old-timers are transformed. After 10 miles of winding its way through countless city streets, our slow-moving peloton hits the wide-open drag of Willamette Boulevard, and impatient riders bolt from the pack. Even Rice takes off , his thick legs transforming into twin pistons, and I have to ride 25 mph to reel him in. Seventeen miles into the trip, when we take a refuel break on Hayden Island, Rice lets me in on a little secret: He rides upward of 7,000 miles every year, and some members average 12,000. “One of our guys cracked 200,000 miles; he’s nearly to the moon by now.”

By the time my ride is over—including nine miles each way to the meetup location—I’ve put in 50 miles, but it’s starting to feel like I’ve been to the moon myself.

[pagebreak]

NO. 6: EAT YOUR VEGETABLES

Outside Natural Selection, a tiny restaurant on a quiet block in the eclectic Alberta Arts District, a sign above the door reminds passers-by: “Eat Your Vegetables.” And once you step inside and surrender yourself to chef-owner Aaron Woo’s four-course prix fixe menu, you don’t have much of a choice in the matter.

Hailed as a “gamer changer” on Portland’s lively vegetarian/vegan restaurant circuit—one of nearly 100 such options—Natural Selection would rather be called a “vegetable” restaurant. That is, it eschews the omnipresent soy and faux meats of its brethren in favor of elevating carrots, parsnips, chard, and broccoli to center stage.

8 Foods That'll Never Make You Fat>>>

“You don’t have to be vegetarian,” says Woo, laughing. “Seriously!” What’s more important, he thinks, is being aware of where your food comes from, how it’s produced, and the journey it took to reach your plate. As such, he strives to source as much food locally as possible, working closely with a handful of Oregon and southern Washington farms that deliver fresh produce directly to his door each week.

The result is amazingly healthy, multilayered dishes—I taste pumpkin-apple soup flavored with fennel, ginger, peppers, and pomegranate; handmade chard and chanterelle gnocchi; and a frisée salad with currants, persimmon, and capers—that are delicious, not to mention indicative of Oregon’s local year-round bounty.

The 20 Fittest Foods>>>

For Portlanders, eating healthy is as easy as sampling that four-season harvest. Thirty-eight local farmer’s markets and 18 community supported agriculture (CSA) programs sell produce direct to local consumers. Hundreds of Portlanders raise small livestock—pigs, goats, and the like—in their yards for dairy and meat, and thousands raise chickens. Whole Foods and the local grocery chain New Seasons Market devote huge portions of retail space to homegrown food. Cherry, apple, plum, fig, and pear trees, once part of local orchards, burst with fruit on residential streets. Famed farm-to-table restaurant Meriwether’s grows 15,000 pounds of its produce on Skyline Farm in northwest Portland. Even City Hall, under Mayor Sam Adams, converted its impeccable lawn into a 700-square-foot veggie garden. Add to that the many vegetarian joints…

11 Green Foods for Every Dude's Diet>>>

All this leads to Chef Woo seeing more vegans, vegetarians, and generally health-conscious eaters here than anywhere else he’s lived or visited. “I think Portlanders are a little more conscious of what they eat, what they buy, their lifestyle,” he says. “I think the small-city nature of Portland allows that. It allows you to slow it down and be a little more aware in general, to make more conscious decisions.”

In the same way that you’ll have a hard time getting in shape while adhering to an unhealthy diet—no matter how hard you work out— whole-foods awareness, and of course, actually having access to healthy food, is important to a fit city.

NO. 7: NOBODY'S PERFECT

Some Portlanders are—gasp!—fat. In fact, the obesity rate here is 25%, higher than any other city that cracked our top 10 Fittest Cities. Beyond its addiction to high-alcohol, high-calorie craft beer—Fed by 53 breweries, more than any other city in the world—Portland suffers from a gut-busting penchant for greasy bar snacks and down-home fried foods. Witness the fattening—and delicious—fried chicken biscuit sandwiches at Pine State Biscuits, the annual Baconfest, and most famously, the line snaking out the front door of hole-in-the-wall shop Voodoo Doughnut.

America's Top 10 Craft Breweries>>>

I stood in that line to get a taste of Portland’s most forbidden fruit, the Memphis Mafia fritter. Featured on the Travel Channel’s Man v. Food, this behemoth—a mountain of fried dough stuffed with banana chunks, then glazed, sprinkled with cinnamon sugar, drizzled with chocolate frosting and peanut butter, and topped with crushed peanuts and chocolate—is a nod to Elvis Presley’s entourage. I’m no dietitian, but the Memphis Mafia seems like exactly the kind of fitness-fueling energy I need, so I buy two.

The 8 Absolute Worst Foods to Pump into Your Body>>>

Truth is, Portland’s obesity rate is a good reminder that no city’s perfect. Other highly ranked burghs had blemishes on their records, too. Both No. 6 Washington, D.C., and No. 13 Miami rank among the 10 most overweight cities. Many residents in No. 4 Denver don’t have great access to healthy foods. No. 8 San Diego and No. 9 Atlanta aren’t bike-friendly.

The point here is that many factors contribute to whether a city is fit or fat. In the end, where it falls on our list is a matter of how well it can balance geographic strengths and weaknesses with cultural priorities and good policy.

So, yes, Portland has its deep-fried dough-cinnamon-banana-chocolate-peanut butter fritters, and enough beer to get the entire country sloshed, but it’s also the best place in the whole country to burn it all off.

The 14 Worst Things You Can Do for Your Body>>>