This is not good.

Not good at all. Lots could go wrong on this one. Cops. Beaten and robbed. Stranded. Definitely the worst ride yet. Shouldn't have gotten in this van.

I glance over at Ethan. He's looking straight ahead. Even his pet rat, Echinacea, is still. I roll another cigarette and inhale deeply.

We're sitting in the middle of a large maroon van driven by a balding Latino guy named "Blue" who has been in and out of prison for the last few decades, mostly for armed robbery. In the passenger seat is his hustling partner, L.A., named after his city of choice, where he also did time. Both have jailhouse neck tattoos. I suspect L.A. carries a gun under his big Tupac shirt.

In the back of the van is Courtney, Blue's girlfriend. She's wrestling with two of their boys — one of them a long-lashed kid with a killer smile, the other still in a baby seat. Courtney's pregnant with Blue's third child. The kids scream and yell, and she screams and yells back. Blue has a habit of calling his child "nigga."

For the last two hours, we've been riding in this van while they hit every Wal-Mart between Orlando and Kissimmee, stealing merchandise and then returning it (without a receipt) at the next Wal-Mart for gift cards. Then they take the gift cards, use some of it for gas at the Wal-Mart filling stations, and take the balance in cash. That's been their hustle for the last four years.

Why they decided to pick us up at a gas station outside Orlando is anybody's guess. Maybe they wanted us to help. Maybe we were the decoys if the cops showed up. Maybe they liked our company. No, not that last one.

We made it clear we weren't going to help them, but once inside the van we were pretty much in for the long haul. Just get us to Tampa, I said. We've been on the road for four days. Ethan needs a shower and I need a real bed.

Blue and L.A. talk in hushed tones over the gospel rap blaring through the car speakers.

"Naw, man, they've been loyal," I hear L.A. mutter. Is he talking about us?

"Well, you wanted an interesting ride, right?" Ethan says softly.

Yeah, but this wasn't exactly what I bargained for when I agreed to hitchhike across Florida with a traveler kid named Ethan Clarkson and his pet rat. Then again, what did I expect?

The act of sharing transportation has been around as long as there has been transport to share. Even the Bible has a story about a hitchhiker: the apostle Philip, who takes a ride from an Ethiopian eunuch on a horse in the New Testament.

In the United States, hitchhiking took hold during the Great Depression when a generation traveled by thumb and by train looking for work on farms and factories. But it was Jack Kerouac's traveling opus, On The Road, published 50 years ago this year, that romanticized hitchhiking for the masses.

Hitchhiking went from being just an alternative for the poor and carless to a form of adventure, or even a political statement, for counterculture types and societal dropouts. And for countless authors and screenwriters, the idea of riding with a stranger on the open road has conjured up oddball characters, enlightening encounters and, of course, rides from hell.

Urban legends of rape and murder still hover around the act of hitchhiking, the result of the media hype surrounding a few grisly incidents in the 1970s and '80s, and, of course, paranoia-inducing horror movies like The Hitcher.

Such are the warnings I heard when I announced my plan to travel Florida by thumb. Hitchhiking in the '60s was OK, people told me. But in 2007? No way. There are crazies out there.

Yet 50 years after Neal Cassady and Devon Smith (who held the Guinness Book of World Records title for most miles hitched until 1985), a new generation of disaffected youth has taken up the mantle of thumbing for free rides. Blending a distrust of suburban respectability with a love of punk rock and radical politics, these new "traveler kids" regularly traverse the country. Through touring punk bands and radical organizations like Food Not Bombs, they've formed a tightly connected subculture, offering fellow travelers places to stay, free food and camaraderie. They've written far-circulated books like Evasion, the story of a punk who steals and scams his way across the country, and have begun websites like and

About a month ago, one of those traveler kids ended up on my couch. Clarkson, a 25-year-old photographer from Iowa, claims to have traveled 28 states in 16 months, covering nearly 15,000 miles via hitchhiking and train-hopping.

Stuck in St. Petersburg after his would-be host left town, Clarkson, a friend of a friend, found his way to my pad with his friendly, cream-colored rat, Echinacea, telling stories about his days hanging with Detroit punks, squatting abandoned high schools in New Orleans and bumming around Brooklyn with an anarchist rabbi named Shalom. The tales would be hard to believe if not for his photos.

"I think traveling is the most effective way I can build a portfolio and see the country," he says about his decision to leave home in March 2006. "I spent 24 years in one state. I had gotten everything out of Iowa that I could possibly get. I think traveling is the most amazing thing I've done so far."

The college-educated artist began posting his travel photos on a personal website,, partly for himself and partly for his worried family and friends back home.

"It's kind of like a political statement, too," he adds. "I'm not going to drive a car, I'm not going to work and pay your taxes. I'm going to be totally free."

The more Clarkson talked, the harder the traveling bug bit me. I'd done a few cross-country trips by car and bus, but never anything as risky as hitchhiking. So, while sipping whiskey at a neighborhood bar, I proposed an idea to him: Take me with you hitchhiking for a weekend. He agreed on the spot. Two weeks later, we packed our bags for a free ride through the heart of Florida.

Water bottle: check. State ID: check. Sharpie marker for signs: check. Extra pair of socks: check. Blanket and tarp: check. Map: check. Half a roll of toilet paper: check. Knife: check.

I throw on a pair of jeans and thin blue shirt. Clarkson wears the same drab cargo shorts and stained white T-shirt he's worn for weeks.

It's been raining since sunrise, and we're hurrying to make up the lost time. Clarkson doesn't give me any hitchhiking tips except for rule No. 1: Never leave your pack. No matter if we're at a rest stop and you just have use the bathroom. No matter if it offends the driver. A hitchhiker never leaves his or her pack.

"Without your pack," he warns, "You are pretty much naked on the side of the road."

Around noon, we make it to the headquarters of Creative Loafing newspaper in Tampa. A classified rep gives us our first ride, to Bearss Avenue off I-275. As soon as she speeds away, we realize the mistake.

"This is a bad spot," Clarkson says. No truck stop. Barely enough space on the shoulder for a car to pull over. No cardboard sign. "This is a real bad spot."

Undeterred, we get on the grassy median by the on-ramp heading north and do what countless others have done before us: stick out our thumbs.

I feel a little silly. The stares from passing drivers add to my discomfort. A Pasco sheriff's deputy drives by. So do at least two dozen cars. Then, without warning, a black Tacoma truck pulls over. We jog toward it.

"Hop in," a strong-jawed man with a blond military crewcut tells us. "Where you heading?"

"Gainesville," we answer.

Our Good Samaritan turns out to be Link, a 36-year-old property manager and Marine who fought in the first Gulf War and has just returned from three tours in Iraq. A stark black tattoo of an AK-47 with the phrase "Death before dishonor" in Sunni Arabic marks his forearm. In his spare time, he traps alligators.

"I usually don't pick up hitchhikers," Link says, a refrain we'll hear several times on the trip, "but you guys don't look like killers."

He shoots us a grin.

Link drove supply trucks from Kuwait through the Sunni Triangle. He was discharged this year after he drove over an IED.

"Everything in the back of the truck came into the cab," he recalls. "And I wasn't carrying anything special. Just food and water."

Link carries on about Iraq for the next several miles. He talks about the unguarded weapons at U.S. bases, the infidelity of significant others back home, the nightmares.

"You're lucky there isn't a draft," he continues. "You don't want to go to Iraq, man."

Link turns up Hank Williams Jr. as we pull into an Ocala truck stop. This is our stop.

At the next on-ramp, I'm more confident, standing in front of Clarkson and smiling as I stick my thumb toward the road. I'm having fun: the adventure, the characters, the adrenaline that shoots through you when someone stops. I could do this all day; Clarkson says we might have to. Thirty minutes crawl by. A sheriff passes but doesn't stop.

Hitchhiking is legal, according to Florida state law, although people are prohibited from walking on interstate highways and must stay on the on-ramp shoulders. However, some cities and towns have their own ordinances, and that's where you get into trouble.

"Usually they're pretty cool," Clarkson says about law enforcement. Some officers will even give hitchhikers rides to the next county "just so you're out of their hair. I've gone several counties in a row that way."

He takes out a harmonica and I share my dirty hitchhiking secret: Once, as a teenager, I mocked a hitchhiker with a thumbs-up while driving by laughing. Clarkson shakes his head.

"That's the worst thing you can do," he lectures me. "And the least original."

Sure enough, in the next few minutes, a group of teenagers give us the thumbs-up as they speed onto the interstate.


A few more cars blow past before a green Ford pickup truck pulls onto the shoulder. The driver, a wrinkled fellow with a mullet, points to the back of the truck. We jump into the dusty pickup bed, wedge ourselves next to a generator and toolbox, and head down the road.

"These rides are nice sometimes," Clarkson says. "You don't have to talk. You can just rest."

Which is good: I'm still exhausted from trying to entertain our first ride.

"Stories," Clarkson says. "That's all we have to offer these people."

Our kindhearted hillbilly hauls us right to the University of Florida campus. Clarkson, during one of his earlier trips through Florida, met a group of traveler kids staying near campus. He figures we can talk our way onto a couch and maybe into a party, but when we reach the ramshackle shotgun house, his friends aren't there. Ironically, they're traveling themselves. We spend the next three hours at the local Checkers. Clarkson calls his mother.

Once darkness falls on the summer-weary college town, he uses his Slingshot Organizer — a kind of national guidebook to anarchist-friendly people and places — to find Wayward Council, a DIY punk-rock venue. On this night, they're hosting four touring bands. Outside the club, I chat up the organizers while punked-out college girls surround Clarkson, intrigued by his rat. A street kid with a mohawk and thick Southern accent sits by us. Clarkson distances himself. "Heroin addict," he whispers.

"I can talk to 10 travel kids, and I'm guaranteed that one of them, if not four of them, will know someone I know," he says. "There are a lot of travel kids. Even in the last six months, I've seen more than I used to. Not all of them are cool. A lot of them are escaping something."

After the show ends, we find a vacant lot surrounded by oak trees and lay out our tarps. I use my backpack as a pillow. Sleep comes quickly. The trip is starting to feel less like hitchhiking than just being homeless.

As the sun rises atop the trees, we roll up the tarps and head to Waldo Road. Ten miles down is the Waldo Flea Market, an open-air bazaar featuring 1,000 of Central Florida's finest dealers of junk, Clarkson insists.

We're barely on the road 10 minutes with our thumbs out and a crude cardboard sign announcing our destination before a Jeep carrying two Hare Krishnas stops. The driver says something about karma and remains silent.

"I've had cars that pick me up, and they don't talk," Clarkson says later, "and that makes me nervous."

When we reach the flea market, I feel like I've reached Conrad's "Heart of Darkness." Savages with mullets of all sizes peruse the tables of collectible guns, knives and "Bible Bread." At one booth, a man resembling Yosemite Sam drags a small black puppy he's affectionately named "Nigger" across the floor. But the most unsettling part of the collection is in a large tent at the edge of the property: Redneck Country features all the Confederate flag stickers, shirts and tank tops any Central Florida yokel could want. And, at the back of the tent, a vast collection of Klu Klux Klan and Nazi-themed memorabilia lines the wall. A country song about lynching blares over the speakers.

Suddenly, Waldo doesn't seem like such a great place for two young hitchhikers. Or a reporter. Clarkson quickly spots two teenagers on their way out of an antique booth who agree to give us a 30-mile ride in their Honda Civic up U.S. 301.

Our rescuers, 18-year-old David and 19-year-old Britney, live in the small town of Keystone. David, a large guy with a mop of brown hair, plays guitar and myriad other instruments ("There isn't that many people to play with in Keystone," he says), and Britney enjoys getting intricate gothic tattoos. They don't mind the rat running around their car.

"It tends to be poor people that pick you up or people who used to hitch," Clarkson says. "Old hippies. People who have ever been on the side of the road and wished someone would stop."

He thinks for a minute and adds, "Or it's the people who are bored."

That seems to fit David and Britney; they decide to take us an extra 20 miles. ("We have nothing else to do," David says.) They drop us off at the intersection of U.S. 301 and State Road 100, which will lead us straight to the east coast. Almost immediately, a Brooklynite named Jensen gives us a lift. Returning to Jacksonville after a construction job in Gainesville, Jensen ran out of gas a few miles back and had to pawn his tools for the gas money home.

"You can rob me if you want," he says, looking back at me. "But I got no money. It wouldn't bother me, though, if you did."

Jensen drives as I imagine Neal Cassady must have: swerving maniacally, yet fully in control. He's going at least 30 miles over the speed limit, and he always seems to be looking at us, not the road.

Jensen talks rapidly about the million dollars he earned through investments in his early 20s and how he squandered it all on cars and cocaine. He's an animal lover but vaguely racist. When we pass a black hitchhiker, he smiles: "Sorry, brother."

He takes us only 20 miles and promises to come back for us, but after he speeds off, our thumbs attract another kind driver.

Amy, a single mom and community-college student, pulls her blue Chevy truck over and motions for us to hop in the back. She's going right into Daytona Beach for a ride with an ambulance. ("It's for school," she says.) Once we're settled in, she hands us two Capri Suns.

An hour later, we reach the beach and run toward the Atlantic Ocean in our boxers. It's our first bath in two days. But our celebration soon ends. Rain clouds from the west move in quickly, and within the hour we're under a Kangaroo gas station awning while the skies pour their fury on us. This isn't going to be an easy night. Where are we going to sleep?

That's when we meet the Pirate.

Dressed in a pair of tattered shorts, his stringy blond hair poking out of a bandanna, John looks the part of a pirate. Faced with no other choice, we take him up on his offer of a motel room. At least until the rain stops.

"I got into some money lately and I'm visitin' my daughter this week," he begins in a thick Rhode Island accent. "I do that three or fo' times a yea'. I got two guys f'om the pawk stayin' wit me already and some girls are supposed to come by, but you can hang out as long as you want."

I'm a little suspicious; Clarkson is giddy. "I love being adopted," he says.

Inside, the Pirate introduces us to the Irishman, a homeless Vietnam vet of Irish descent, and the Caveman, so named because the unkempt black beard that covers his face reminds the Pirate of a certain Geico commercial.

The Pirate found his vagrant friends after work one day and offered them a place to stay out of the rain. He was supposed to return with girls and rum, his new friends admonish him. Instead he brought back stinky hitchhikers.

While the three men pass a bottle of whiskey, Clarkson shares his cross-country adventures. The Pirate and the Caveman think he's crazy for hitchhiking, but the Irishman understands. The vet tells us he's been to every state and over 20 countries. He urges Clarkson to continue his travels.

One by one, the men pass out. Clarkson and I decide to crash on their floor. Tonight, we'll stay dry.

The next morning, we bid farewell to our new friends and spend the morning on the beach. By noon, we walk seven miles to the I-4 on ramp, confident we'll make it to Tampa before nightfall.

Hitchhiking rule No. 2: No guarantees.

We leave Daytona Beach with a couple on their way to the Orlando airport. But much to our chagrin, they drop us off in the suburban hell of Altamonte Springs. All the buildings look the same. So do the cars. And everyone stares at us like they've never seen hitchhikers.

Within 15 minutes, two Altamonte Springs police officers yell at us from their patrol cars to get off the on-ramp. As we walk down the road, four more police cars pass us slowly.

I secure us a ride at a gas station with a man heading just two exits up to a more desolate, wooded area outside Orlando, but our bad luck continues for two hours. My thumb actually starts to cramp. Seven different cars give us the mocking thumbs-up. I hate Orlando.

As the sun dips behind the trees, we call it a night. People don't pick up hitchhikers at night, Clarkson says. Exhausted, we make camp in a group of bushes in front of a Motel 6 a few miles up the road. I watch a hooker get out of a truck. I force myself to sleep.

When I return with coffee the next morning, sheriffs' deputies have Clarkson surrounded. One questions me while another searches my backpack. Clarkson, according to the authorities, fits the description of a drug dealer. But after the cops run our licenses, he's let go — just in time for a huge thunderstorm. We spend the morning under an overpass.

When the rain dies down to a sprinkle, we head to a gas station to ask about the nearest truck stop. Maybe we'll have more luck on the other side of the city. It's already 2 p.m., and I'm beginning to think we'll be stuck in Orlando forever. That's when the van of thieves pulls up next to us, offering a ride to Tampa.

We have 40 miles behind us when a Wal-Mart employee, suspicious of Blue, refuses to return his merchandise. He walks back to the car, his face red and puffy.

"Motherfuckers," he mutters. "They got some uppity Wal-Marts around here. We need to go back to Orlando."

I protest. But Blue dismisses me.

"I know a few stores in the ghetto that'll take this stuff," he says. "Then we'll be on our way to Tampa."

The kids in the back start screaming again. Blue turns up the gospel rap.

After hitting the second Wal-Mart in Orlando, Blue hands us a gift card, telling us to grab some food and cigarettes for the ride into Tampa.

"We'll be back before you're finished," he says. "We have to make a deal with this guy and he can't see you."

I look at Clarkson and nod. I open the van door, step out and then glance back. Never leave your pack.

I reach in and hoist it on my back. Clarkson follows my lead.

"Why you taking that?" L.A. asks, but I don't answer and close the door.

The van never comes back for us. The gift card is empty.

"That's the worst ride I've ever had," Clarkson says.

Worse than the heroin addict that shot up in front of you?


Worse than the guy who propositioned you with a 10-inch silicone dildo?

"Him, too."

I take out our map. The closest highway is the Florida Turnpike, more than 10 miles away. I-4 is even farther. The sun is setting. We're stuck in another Orlando suburb. I have to be at my desk tomorrow, and there's no way I'm spending another night in the bushes. I break down and call my roommate to come get us. I'm a weekend warrior. Traveler kids hate those.

Sitting on the bench, Clarkson recaps our adventure. "What do you think," he asks, "about hitchhiking?"

"Well …" I think for a minute. "It's better than the Greyhound."

When I see my roommate's car, I step to the curb and stick my thumb out.

"Where ya heading?" she asks.


"Hop in."

More by Alex Pickett


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