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Tree riding illustration
(Illustration: Shout)
Tree riding illustration
As the tree slowly went down, the rider would balance his legs on the trunk until he could let go and stand up for the couple of seconds it took to reach the ground and jump off. (Illustration: Shout)

My Adolescent Jackassery Can Be Summed Up in Two Words: Tree Riding

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How boredom and booze created an outlaw sport best left alone

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Over the course of my professional life, I’ve heard the maxim “Success happens when preparation and opportunity collide” more than a couple of times. It usually accompanies a big-hearted “Congrats!” when I leave one job for the next “adventure,” as we pretend jobs are on LinkedIn. A motivational-speaker guy named popularized that nugget, the live-laugh-love of the corporate world, although the internet tells me it was derived from something that Seneca, the Roman Stoic philosopher, once said.

Anyway, Zig, bless his soul, seemed like a nice fella. And I do agree with him to an extent, as a forty-something father now, with my own troops to rally. Plus, like me, he grew up in Mississippi, and we mostly stick up for each other here—outside of . I don’t mean to besmirch Zig’s legacy of motivational books and whatnot. But for the sake of this story, I’ll instead say that “Tree riding happens when boredom and booze collide.” Or maybe just “Tree riding happens when boredom and boys collide.”

We’ll get to tree riding. But first we’re going to , Mississippi, a small, postcard-pretty town along the Gulf of Mexico. Ocean Springs is best known as the laid-back home of the late watercolorist and naturalist , an eccentric who would row his skiff to uninhabited Horn Island, a dozen miles offshore, to paint landscapes and wildlife. Before Ocean Springs became a destination for artsy types and vacationers staying at casinos on the other side of Biloxi Bay—all drawn by a downtown lined with shops and bars and restaurants—it was a quiet place intermittently interrupted by kids like me and my friends on skateboards and BMX bikes.

Faced with a lack of real oppression in our own Mayberry, we excelled at creative recreation in our teenage years. Occasionally that meant flouting authority by leaping off bridges, jumping out of speeding boats, maybe knocking down mailboxes, if the statute of limitations on that has passed—you know, gingerly riding the line between mischief and delinquency but mostly staying out of trouble. We were feral nineties kids, the last generation to roam neighborhood streets and wooded lots until the streetlights came on, and we have the scars to prove it.

Only a place steeped in adolescent boredom could produce a sport so maddeningly stupid as tree riding. And when I say tree riding, I’m not talking about riding a bicycle through some woods. I mean actually using a tree as a thing to ride. In this case, the place you rode to was the ground, and the trick was to not smash your face into that ground, or the tree’s trunk, when you arrived.

A typical session went something like this: Four or five of my friends and I, sometimes more, would stumble into the woods and find a suitable specimen, a climbable tree maybe 20 feet tall, 30 tops—usually a coastal pine or a small oak. One of the guys would shimmy up the tree while another went to work with a saw. As the tree slowly went down, the rider would balance his legs on the trunk until he could let go and stand up for the couple of seconds it took to reach the ground and jump off. Then we’d laugh and open another beer.

Before you dismiss this as simple redneck buffoonery—which, I admit, it was—be aware that our bumpkin bona fides were slim. We were townies, not hicks; we would choose a skimboard and a Gulf breeze over popping squirrels with a .410 in the woods. But it’s a lot easier to get away with felling trees in the boonies than in your neighbor’s front yard. So when it was tree-riding time, we headed into the county east of town, where the sun-baked pavement drills a straight line through flatlands filled with tall, narrow wisps of pines planted after the paper companies logged the virgin growth decades earlier.

Out there, the roadbed rises a few feet higher than ditches on either side, hovering just above sea level; beyond those ditches, low, sandy soil stretches in every direction. A rural road called Fountainbleu led us to a network of singletrack trails snaking around the bayous and expanses of marsh grass, hidden from the few passersby behind trees and the scrubby yaupons that fill the understory. From a distance, this is some of the most striking, serene coastal marshland you’ll find anywhere, with sandhill cranes, pelicans, and seagulls standing stoically and soaring majestically over swaying fields of reedy grasses and cattails. Get too close, though, and you’ll see the alligators, cottonmouths, and wild hogs that dominate the ecosystem. Merciless, blood-sucking deer flies will chase you out if those fail to intimidate you.

Into these woods we drove, intentionally, in search of adventure. Before any of us had licenses, my buddy Mike would swipe the keys to his parents’ , a green bomber worn to primer in places and rust in others, with a dingy white top and a hole in the dashboard where a stereo should have been. It also had a sticky accelerator, which we discovered during one infamous country joyride. As we rumbled toward a dead end enclosed by a wall of trees, Mike swung around and backed into a sandy roadbed, then floored it to see how much sand we could throw with the rear wheels. We didn’t bank on the gas pedal seizing in the oh-shit position, fully flush with the floorboard.

The Nova shot through a cloud of sand and smoke at a surprising rate of speed—there was no way to tell exactly how fast, due to its wobbly speedometer and the chaos of the moment—and we were suddenly in uncharted territory, yelling at Mike to stop while all 250 cubic inches of engine screamed louder, and the roar reached an unnerving pitch higher than you ever want to hear from a one-ton, combustion-fed machine. He finally slowed the car by holding down the brake pedal with both feet while the rest of us bailed, leaving him alone to wrangle the angry beast into submission. Which he eventually did by slamming the transmission into neutral, then park, and then shutting off the engine.

We were feral nineties kids, the last generation to roam neighborhood streets and wooded lots until the streetlights came on, and we have the scars to prove it.

Once we all reached legal driving age, the Nova suddenly changed from a revered symbol of freedom to a tangible thing. It became a proper noun—The Nova—and it whisked us noisily wherever we wanted to go. Two-hour road trip to Gulf Shores on a whim? Sure. Need to get to the mall to buy concert tickets in afternoon traffic? We’ll take the shoulder. Is that a stop sign? Bam! Now it’s a hood ornament. And the pièce de résistance: two small escape hatches where the rear floorboard had rusted out, in case we needed to ditch any contraband. It was like having the coolest fort you could build, but on wheels that could take you places like the Saint Andrews Trails between Belle Fontaine Marsh and Graveline Bayou.

The Saint Andrews Trails were made for trouble. Rednecks loved mud riding there, and they made sure everyone knew it by leaving the orange-brown clay cemented to their trucks for weeks after a run. On weekend nights, cars lined the road by a burned-out house and teenagers drank cheap domestic beer in clusters, mingling in the light and shadows of car headlights. It was all forbidden enough to entice our young minds, not to mention lawless, if our encounters with Jackson County deputies were any indication. Most of the time, if you were respectful to them, they were content to watch you pour out your beer and send you home. It was a hedonistic playground behind “Posted” signs. It was the perfect place for tree riding.

There are many days in our youth that we can look back on and say were important. Some seem so inconsequential in the moment, a “minor, insignificant preamble to something else,” to quote , my generation’s Easy Rider. But then, once the rest of our life reveals itself, those moments bear the weight of significance. One Saturday, Mike picked up me and some other friends in The Nova, and we met a truckload of other friends and all ended up at the trails.

It had rained the night before, and the dips in the sandy road were now ponds of water the color of café au lait, with no way of gauging how deep they went. Luckily, we had Brent and his eight-cylinder 1977 Ford F-100 pickup, which was riding on 30-inch tires. He plowed into the muck, sending impact waves arcing out from either side of the chassis. Mike did his best to avoid it all, but The Nova took a mud bath anyway, and some of it seeped up from under the floorboard. We spun out in this thick, unholy union of rainwater, sand, clay, and swamp mud, fishtailing from one hole to the next until Brent decided to stop.

The first guy to go up a tree was Brent’s little brother, and what happened next is fuzzy, but I can tell you he botched his ride so badly that he later had to get stitches on his head. “Nothing a few beers won’t take care of,” one of us probably said, again in reference to our favorite movie.

My wife likes to say that when my friends and I get together, someone’s getting hurt or getting cited. My friend Byrd was reliably game for either, and by his turn he was half in the bag, his limbs all loose and lubed thanks to a few Silver Bullets he drank during the drive. He shimmied up the pine, shucking some of its flaky bark along the way, and stopped about ten feet above the ground as two other reprobates dug the saw’s teeth into the tree he had climbed and now clung to. When it started to fall, he began to stand up, but suddenly the tree stopped moving.

Byrd turned around to ask the guys what the hell they were doing, but he only got out the first two words—“what the”—before the tree resumed its descent. He hadn’t gotten back into position when—smack!—his chest smashed into the trunk, bounced back up, and then slammed down again. He lay there quietly for several moments assessing the extent of his injuries, while we tried to stop laughing, and then rolled off the trunk and eased himself upright, knees where his feet should be. Byrd had a helluva time explaining to his parents how he got the scrapes and the massive bruise that spread over his chest.

I can’t say tree riding ever became popular. As far as I know, we were the alpha and omega of the pastime, at least in our corner of the world. I would like to say we learned our lesson after all the injuries, yet that isn’t entirely true: we still had college ahead of us. But slowly we aged out of flinging ourselves at danger and lived to help create our own little people—people who will not get away with anything, ever. Sorry, kids.

The geniuses responsible for this sub-Olympic sport live and work among you now. One became an emergency-room physician. People call him doctor, and he sews up dumbasses like our younger selves for a living. Another became a lawyer who defends clients for more serious versions of the petty stuff we used to get away with. And one became a full-time adventurer who owns a few whitewater-rafting companies and spends the off-season cheating death in new and novel ways.

After surviving the trials of adolescence together, I can’t shake a sense of wonder at how we all made it without having a résumé marred by red flags and redactions. But now I know Zig had it right all along—preparation does come in handy when opportunity, or at least an emergency, strikes.

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Lead Illustration: Shout