The city of Jaisalmer protrudes from the Thar Desert like a dirty iceberg encircled by herds of wild camels. The desert sandstone city, an hour from the border of Pakistan, is built around an 858-year-old fortress within whose walls about 4,000 people still live. With only eight inches of rain each year, nothing grows more than knee-high.

On this late December day, however, the streets are populated with sweaty young Westerners sizzling under the sun in delirious costumes—Bananas in Pyjamas getups, Union Jack suits, Where’s Waldo? outfits. Locals on soapboxes try to lure them into street stalls, but these Westerners aren’t here for sightseeing. They’re here to race.

I’m here looking for a ride. The sweltering city is the starting point of the Rickshaw Run, a daring and dangerous 2,200-mile trek down the entire western flank of the world’s second-most-populous country in a three-wheeled, seven-horsepower piece of shit with a fickle lawn-mower engine. Eighty teams have flooded in from Norway, Taiwan, Philippines, New Zealand, Italy, Ireland, Belgium, the U.S. and especially England and Australia. Today is my chance to jump in with any crew willing to take me along.

Brightly painted rickshaws cluster in the sandlot, but the vibe is far different from the starting line of a Formula One race. For starters, the thin metal exterior of a rickshaw feels about as sturdy as the coin-operated airplane rides outside grocery stores. Teams who submitted their paint-job designs ahead of time arrive to find local artists’ liberal interpretations. The pale, cherubic portraits of three oil-rich Norwegian teens have come out decidedly darker, with thick unibrows and longer sideburns than they’ll ever be able to grow. Australian siblings prep a rickshaw with a swirly tie-dyed pattern complete with a levitating portrait of a wasted-looking Rick James. Tassels, lights, flowers, streamers and a disco ball hang from the black vinyl roof. As I cross the lot, ice-cream-truck jingles fill the air, emanating from a rickshaw covered in ice-cream-cone graphics and surrounded by Kiwis handing out frozen snack bars.

1) The Adventurists’ literature warns of being “seriously injured or dying as a result of taking part.” Here, Matt Dickens outlines a list of military zones to avoid during his prerace speech. 2) The Rickshaw Run’s starting line in Jaisalmer, an 858-year-old sandstone city. 3) The rickshaw motor is a fickle beast, particularly the carburetor.

This is the “pimping” portion of the morning’s race preparations, when teams can outfit their vehicle. Once the test-driving begins, so does the shit show. Sand swirls as drivers take in a five-minute crash course that covers how to start a rickshaw motor with the elbow-slamming hand lever that juts from the floor. Runners jam the grip shift into first gear and rip donuts in the hot dirt, stalling, running out of gas and crashing into bystanders. The hotel staff, clad in green Nehru jackets and orange turbans, weaves through the chaos, carrying silver platters loaded with discretionarily priced beer.

While I weigh my options, a team of American girls is busted for breaking an ambiguous traffic law. It is enough for a cop from the local traffic ministry to threaten to shut down the entire event. For a minute it appears as if the Rickshaw Run is over before a single tuk-tuk hits the highway. A series of discussions ensues, and the officer is eventually bribed, rather easily, with a new laptop. The Rickshaw Run will go on.

“Our humble little planet used to slap us humans about the cheeks with iron fists of adventure every single day” is the pitch used by the Adventurists, the irreverent British company behind the Rickshaw Run. A major downside to societal progress, it claims, is the exploitation of “adventure” as a marketing catchphrase for luring tourists. The company aims to cater to a growing class of travelers who no longer get kicks backpacking through Europe, following the same Lonely Planet guidebook as everyone else at the local hostel.

For average tourists, “their day-to-day activity is staying in hotels and eating in restaurants,” says Tom Morgan, the 35-year-old founder of the Adventurists. “They could just wander the world aimlessly—or take on the challenge of driving a highly inappropriate vehicle across India.” Morgan has made a life of adventure. “I’m from Chichester, the least exciting town in the whole U.K.,” he explains. “I had a deep-seated desire to escape.” At the age of 12 he built a wooden airplane to fly to the jungle, and as a teenager he backpacked around Africa, getting robbed in Zimbabwe and trapped at the border in Mozambique.

“It was only when things went seriously wrong that I enjoyed it the most,” he says. An art major in college, Morgan formed the idea for the Adventurists after a disastrous 2001 road trip from the Czech Republic to Mongolia in a Fiat 126. He organized the first Adventurists event three years later: a 10,000-mile race to Mongolia from various parts of Europe. Four teams entered.

Today, the Mongol Rally attracts nearly 300 teams from more than 20 countries, and the Adventurists has grown into a maniacal outfitter for people who want to scare the shit out of themselves while traveling. There’s the Ice Run, which sends participants down a 1,200-mile frozen river in the subarctic Siberian wilderness on a Soviet-era sidecar motorcycle. The Mongol Derby re-creates Genghis Khan’s 600-mile postal route across rural Mongolia on native horses. And there’s the Mototaxi Junket, off-roading the length of Peru on a motorized tricycle through the Andes and across the Amazon basin.

The Adventurists’ website warns, “Your chances of being seriously injured or dying as a result of taking part are high. Individuals who have taken part in the past have been permanently disfigured, seriously disabled or lost their life. You really are putting both your health and your life at risk.” There are plenty of crashes, injuries and even problems of international diplomacy. One team spent 28 days stuck at the Russian border, all the while refusing to give up. A rickshaw team trapped in the middle of riots in Bihar, India survived to find an arrow stuck in the side of its vehicle. The Adventurists’ guiding principle is that there is no pretense of smooth sailing. Expect things to go very wrong, probably in a very remote location.

The company is no less chaotic. Based in Bristol, U.K., with remote employees in Mongolia, Peru and India, the outfit stages events that are remarkably disorganized—a suitable precedent for the whole experience. A handful of teams show up in Jaisalmer to find that their rickshaws haven’t. Several motors won’t start. These are minor reminders of the disarray and breakdown of order that lie ahead.

“India is like a fucking acid trip. Don’t try to control it. You will lose.” This is the best advice Matt Dickens, chief of the Adventurists’ India branch and unofficial Willy Wonka, offers on the eve of the race. Dickens’s cavalier presentation brushes over basic rules, the need for emergency medical insurance and a list of military zones to avoid.

The safety warnings are immediately lost as the excitement bubbles over, along with booze. Any mob of people eager to drive wobbly tin cans across India carries rowdy genetics, and soon the frigid hotel pool fills with a crew of chubby Irishmen. The Kiwis begin shaving people’s heads while Australians ink henna tattoos on the faces of passed-out compatriots. A Norwegian throws a wooden chair into the bonfire as a hotel porter beats up a drunken taxi driver who has crashed the party. I wind up sharing a room with a 67-year-old British man who plays a mean blues harmonica but has to be carried to bed three nights in a row, having pissed himself at least once.

There is no set demographic of people who are willing to pay roughly $2,500 to drive three-wheel death machines across India. I meet a group of Swiss policemen, a marketing executive from the Indianapolis Motor Speedway and the coach of Mexico’s Olympic snowboard team. There is a set of identical twin girls being driven by their cowboy-hat-wearing, pot-smoking father, and a pair of American bros who decided the Rickshaw Run was for them after hearing about it from a girl in Belize who was robbed at gunpoint on the previous year’s run. When I ask a 46-year-old Englishwoman with four kids why she is doing the run, she makes a golf-swing motion and says, “My husband is really boring.”

My quest for a racing team actually began several months earlier, in the States. “I’m pretty sure we don’t look like most of the other teams,” Frank Gallina told me via e-mail. “I’m a 37-year-old project manager for IBM, my brother is a 32-year-old bartender from Nantucket, and my father is a crazy 66-year-old paralegal who we hope will survive the run!”

Rail thin, more than six feet tall while slouching and with plenty of type-A neuroses, Frank stands in stark contrast to his brother, Joe, an olive-skinned gadabout who served two years in federal military prison for grand theft auto. Joe is fresh off a solo trip through Pakistan, after which he joined Frank and their raspy-voiced Sicilian father, Frank Sr., who wears golf clothes and quotes Bob Dylan at length.

I join them on Team Marmoset, climbing into their orange rickshaw, which inexplicably features a baby painted on the front. Despite our excitement about hitting the open road, we run out of gas within an hour of the launch ceremony. A gray-haired Frenchman tops us off with his extra can, and soon we are puttering down the dusty road, battling strong morning crosswinds and dodging livestock.

The decision to assist—or not assist—others would become the theme of Team Marmoset’s trek. On the second day, a Norwegian team’s rickshaw sits lifeless on a patch of roadside gravel, and Joe pulls over to adjust their carburetor. A few miles later, someone needs a fuel line purged of a bad oil mix, and Joe squats behind the rear engine compartment, pulling and plugging parts until his forearms are covered in black grease.

Frank Jr. nervously checks his oversize smartphone’s GPS, watching the time and googling hotels. His brother’s mechanical philanthropy is admirable, but it is slowing us down and revving Frank up. “What precipitated today’s breakdown?” he asks Joe late at night. “I read on the blogs that teams are way far ahead of us by now.”

The attention the Rickshaw Runners are attracting becomes noticeable. Men standing wrapped in earth-tone blankets stare at the anomaly: white people, including uncovered women, rolling bedazzled rickshaws over speed bumps while blasting The Chronicand Hotel California on fuzzy speakers.

That’s how we’re cruising several days later, 20 miles south of Ahmadabad, when something slams the bottom of the vehicle and the right rear wheel vibrates loose. Our rickshaw, hurtling along at a solid 25 miles an hour in the far right lane, swerves across three lanes, weaves between two trucks, a hairbreadth away from wreckage, before coming to a violent halt on the narrow shoulder. The dislodged rear axle, blown out of the wheel socket, lies slumped on the ground like a severed limb. Darkness is minutes away, and this rickshaw is going nowhere.

A crowd of spectators forms, including a 15-year-old kid with a mustache and green striped polo. He pokes his hands in, trying to help, only to be shooed away by Joe. Communication is one of the most baffling challenges in India, in part because there are more than 1,500 languages and dialects. (“My guess is that the method of travel you chose and the path you took brought you into contact with people not homogenized by the influences of media and common education and language,” Bhuvana Narasimhan, assistant professor of psycholinguistics at the University of Colorado at Boulder, tells me later.)

With no set route to the finish line, runners have found themselves in the middle of riots, weddings and head-on collisions.

After a few minutes of improvised sign language, our new friend helps jack the rickshaw onto a rock and worms underneath to explain to Joe how to repair the greasy axle. Friends drive him to a nearby shop (which has to be opened), and he returns with the parts and reassembles the axle in the dark using only the light of a small cell phone. Afterward, Joe gives him 500 rupees and they pose for a photo.

Aside from this brief episode, Team Marmoset typically avoids interacting with people. Joe is averse to trusting local rickshaw mechanics, and Frank Jr. obsessively consults his smartphone for hotel reviews and directions rather than ask someone. This isn’t the adventure I want, so I ask to be dropped off in Mumbai, one of the busiest and most densely populated cities in the world, confident I can find a ride.

The incentive to survive the first leg of the Rickshaw Run is the gorgeous, sandy beaches of Goa, where several teams plan to convene—and party. (One Swiss team tells me, “You can ride with us, but we’re going straight to Goa to party for like five fucking days!”) Convincing a mob of Westerners to make the trek in the name of adventure is one thing. The locals aren’t buying it. Rickshaw drivers I ask to take me the 400 miles south from Mumbai to Goa laugh at me. “It is not possible.” “No one will go.” “There is a bus.” “There is a train.” “Rickshaws cannot drive the mountain.” “Very dangerous.” Over a three-hour span, dozens of baffled Indians assure me with visible frustration that this is not a reasonable method of transport. I’m on an adventure, I explain, a challenge with 80 other three-wheelers to drive from Jaisalmer to Kochi.

“You are a crazy man, or you are confused.” Three tall men in business slacks and button-down shirts drink chai from plastic cups on a street terrace. They laugh at my request the first few times I explain it, until an IBM programmer named Rajesh nods, hands me a chai and tells me to follow him. Rajesh power-walks through an industrial labyrinth of pedestrian bridges and metal staircases, then quickly descends to a platform. He pulls me into a blue train car, and we shuffle to the back, where he insists I sit on a bench packed with 10 other men. The Indian government officially refers to this as “super-dense crush load,” part of a daily eight-hour rush of more than 6 million humans. About 500 people cram into train cars meant for 188. That’s 16 people per square meter, or the entire U.S. presidential Cabinet suffocated into a phone booth.

The Adventurists offers three Rickshaw Run “unroutes” every year between Jaisalmer, Kochi and Shillong.

When Rajesh explains my journey to the others, everyone laughs with awkward confusion. “Why do you choose to do this difficult task?” he asks. “Because it lets me do and see things that I wouldn’t otherwise experience,” I answer. He pauses and looks off into some illusory distance. “I understand,” he says. “It’s a great challenge. I admire this.”

It is nearly nine P.M. when I step off the train in the southeastern suburb of Panvel and a young airline worker helps me negotiate my ride. Rajesh advised me to hire a rickshaw outside the city because of strict regulations on Mumbai taxis. The sweaty owner of several commercial rickshaws and 20 young drivers huddle around me as we crunch kilometers and fuel costs and other made-up expenses. The chief of traffic police takes down my information, gives me his phone number and deadpans, “You do this at your own risk. It is not safe.”

The lucky driver who gets the nod is a local man in his early 20s named Salman. He dances with elation at the thought of making more than a few cents that night. Salman recruits another driver named Muhammad to tag-team the journey. The rickshaw comes equipped with blue lights and a 4,000-rupee horn the size of a trombone.

I feel good about our chances of making it to Goa until we stall out three times on the highway entrance ramp and a friend is summoned to clean and tweak the carburetor. Adding to my anxiety is our route along the deadly NH-17, known as the Mumbai-Goa highway. In 2012 this highway saw 193 people killed and 1,290 injured in 1,117 accidents—and those are just the ones reported. That Muhammad and Salman are both professional rickshaw drivers does little to calm me. The International Journal of Occupational Safety and Ergonomics published a study last year on rickshaw drivers’ accident-proneness. The conclusion: “Personality characteristics with lower scores of reasoning, rule consciousness, apprehension and emotional stability are common in commercial auto-rickshaw drivers.” On top of that lovely stat, we’ll be driving at night, which the Adventurists advised us to never, ever do.

On his little cell phone Salman has one song—Michael Jackson’s “Dangerous”— and we listen to the track on repeat until I introduce Justin Timberlake’s 20/20 album, which promptly blows his mind. “This is wondeefool music!” he repeats for each track, bobbing his head with poor rhythm. The moon swings west and Muhammad sings loud Hindi songs, shaking his head to stay awake while Salman and I huddle under a thin sarong for warmth.

I remember that 50,000 vehicles travel this 280-mile highway every day, but bribe-friendly policemen patrol it only from eight A.M. to eight P.M., and most accidents occur between 2:30 and six A.M., when bleary-eyed drivers are least alert and speeding recklessly. The green hands on my black Wenger Commando point to 3:26 A.M. I doze off only to catch myself on the verge of ejection while barreling down India’s most dangerous state highway in the middle of a pitch-black night as Goa draws near.

The minute my feet touch the fine sand on Goa’s balmy Palolem Beach, I am greeted with cheers and beers from a crowd of Australian, Kiwi and British Rickshaw Runners who, having completed the hardest leg of the journey, are ready to party.

Stories circulate about the New Zealand group who killed a jaywalking sheep, leaving them with a dented rickshaw and a debt to a local farmer. Two teams were invited to join traditional Indian wedding ceremonies, one of which was held in an ornate, futuristic pavilion, the other beneath a highway underpass. A group of American college kids unknowingly tried to stay in a brothel, while a Belgian American couple slept in a hospital when they couldn’t find a hotel.

“We’ve met so many great, friendly people,” one Canadian tells me. “Everything from drunk motorbikers giving us their moonshine while driving, to dog attacks, to being dragged into religious blessings.”

For the next leg I saddle up with the ice-cream-coned, sheep-killing Kiwis. We drive for two days past large plantations lined with coconut trees. The guys make for upbeat company, and we spend hours discussing American movies, debating religion and talking about our favorite bands from the 1990s. We sing along to Rolling Stones songs.

“Fawkin’ timeless rawk, ey!” yells one bearded motorhead, fairly jacked up from a cocaine breakfast. I finish the last days of the run riding with two Australian potheads named Nathan and Hayden. An architect and a diesel mechanic, they are the least prepared of any team I’ve encountered, with just a map and no technological lifelines, which necessitates spontaneity. They navigate by pulling over and yelling the name of their next destination, averaging the most consistent response and winging it from there. They wake up later than every other team, take long lunches and yet somehow maintain decent progress.

Earlier in the trip they got lost in a rural town that hadn’t seen foreigners in years. Three young boys on bicycles were sent to find keys to the only hotel in town. The entire village heard of their arrival and showed up to watch them eat dinner, yelling and arguing over what to serve. We are 18 miles outside the finish line when the carburetor dislodges from our engine. While Hayden rigs it back into place with black electrical tape, a chubby boy in his school uniform asks where we are going.

“Kochi,” we say.

“In that thing?”

Up and running again, we sputter past the finish line alongside a trickle of other runners, all expressing a mixture of relief and satisfaction.

“We get more injuries at the finish line because people get so unbelievably annihilated,” Morgan had warned. “We usually have to pay for some sort of damages.”

I can see why. Fire jugglers spit flames at the crowd. Furniture is broken, clothes are ripped off and every drop of alcohol is consumed. Strangers and friends run off to the bushes and bungalows and beaches to hook up, then return, straightening their new Indian clothes.

Bottles and joints circulate, along with stories. An Australian woman rode in a school bus full of 11-year-olds and sang them Boyz II Men songs. A few crews accidentally joined a police escort for the prime minister. Police stopped several teams—not always for bribes but to take photos. The Rick James siblings were featured in a local newspaper along with a photo of them lounging on the beach. A British woman survived a head-on collision that sent her through the windshield, which a friendly man repaired for free within a few hours.

All these outcomes would please Morgan. “It’s for you to decide if the trip is going to be boring or a disaster,” he says. “All we provide is the framework for chaos.”