Happy Trails, Losers: We Asked ChatGPT To Roast Our Favorite Trails, and the Results Are Frankly Insulting

Because nothing says “nature” like having a disembodied robot hurl insults at everything you hold dear, we asked ChatGPT to roast some of our most beloved long-distance trails. Apparently that’s a thing AI can do now.

It took some nudging to get it to do this properly (I kept getting warned that I might be violating the AI’s content policies whenever I asked it to “be meaner,” and GPT proved very unwilling to let go of the image of the Arizona Trail “turning you into an endless dehydration buffet”), but we deem the results sufficiently hilarious/terrifying to share with you, dear reader.

Peace, Love, Existential Dread,

The Editors

Appalachian Trail

“Every ‘thru-hiker’ thinks they’re on some grand odyssey, but let’s be real — you’re just an adult who smells like a foot.”

Wow GPT, wow. Bravo on the aggressive use of quotation marks, honestly. —Eds.

“Oh, the Appalachian Trail, the proud 2,190-mile stretch of rugged wilderness that hikers can’t stop raving about—because nothing says “vacation” like two months of blisters, rain, and questionable food choices.

Let’s talk about that so-called “scenic beauty.” Sure, there are pretty views, but they come with an equal measure of knee-deep mud and bugs the size of small birds. You think you’re escaping civilization, but really, it’s just a long walk to the nearest outhouse, which is probably a glorified hole in the ground.

Those shelters? Sure, they’re a place to rest, but you’ll quickly realize they’re really just crowded, bug-infested communal sleeping bags. Forget about peaceful nights; you’ll be serenaded by the symphony of snoring hikers and raccoons rummaging through your snack stash. 

Imagine walking for six months just to end up in Maine, like that’s the prize. ‘Congrats, you’ve made it through 2,000 miles of bug bites, bear encounters, and questionable trail mix… here’s a state that gets 14 minutes of sunlight a year!’ Every ‘thru-hiker’ thinks they’re on some grand odyssey, but let’s be real — you’re just an adult who smells like a foot and ate ramen out of a Ziploc bag for half a year.

Oh, and can we talk about the people who name themselves stuff like ‘Moonwalker’ and ‘Stardust?’ Bro, you’re not in Middle Earth, you’re in Pennsylvania, dodging rocks that want to snap your ankles in half.

The Appalachian Trail might be hailed as a bucket-list adventure, but let’s be real: it’s more of a brutal endurance test where you’ll question every life choice you’ve ever made while forging bonds with fellow hikers over shared misery.

Happy trails … losers.”

Pacific Crest Trail

“Just wait until you’re 500 miles in, realizing that wifi and pizza delivery are concepts lost to the wilderness.”

Personally it took us over 700 miles to realize there was no wifi out there. And if one more trail angel offers us a stash of half-chewed desperation candy, we are going to absolutely lose our shit. —Eds.

“The Pacific Crest Trail, where Type 2 fun meets relentless masochism. Why take a normal, relaxing vacation when you could instead embark on a months-long quest to lose all hope of ever feeling dry again? Sure, the views are stunning, but you know what’s even better? Showers.

Stretching 2,650 miles from Mexico to Canada, it’s basically a marathon for masochists who find joy in watching their toenails abandon ship one by one.

And let’s talk about the PCT’s famed ‘trail magic’ — more like ‘desperation candy’ from strangers whose idea of a gift is a half-eaten Snickers. Just wait until you’re 500 miles in, realizing that wifi and pizza delivery are concepts lost to the wilderness, and your only friend is that one mosquito who refuses to leave you alone.

Let’s be honest — it’s less about finding yourself and more about losing your will to live. Why climb one mountain when you can climb six, with a side of heatstroke? 

But don’t worry, if the animals don’t kill you, the complete lack of water will. Good luck figuring out if that murky puddle counts as a ‘water source’ or just another reason to rethink your life choices.

And sure, there are some incredible moments of solitude — like when you’re hunched over your camp stove, boiling water for a cup of instant sadness. If you’ve ever wondered what it’s like to slowly disintegrate while pretending to have fun, look no further.”

Continental Divide Trail

“Oh, you wanted water? Too bad—you’re in the desert. Need oxygen? Sorry, you’re at 12,000 feet, gasping for air like a fish on a mountaintop.”

“Like a fish on a mountaintop” just about sums up where we’re at in our lives at this point. —Eds.

“The Continental Divide Trail, or as I like to call it, ‘America’s longest bad decision.’ If you thought hiking was about peace and tranquility, this trek is here to ruin that fantasy in the most spectacular way possible. Imagine walking for weeks through landscapes so remote, your only company is a marmot with an attitude problem.

Oh, you wanted water? Too bad — you’re in the desert. Need oxygen? Sorry, you’re at 12,000 feet, gasping for air like a fish on a mountaintop.

The Continental Divide Trail is like the Pacific Crest Trail’s angry older sibling, with more miles, more altitude, and way more opportunities to regret your life choices.

And don’t worry about navigation — most of the trail is ‘choose your own adventure’ because, you know, who needs signs? Half the time, you’re wandering through wilderness like some lost toddler, hoping that cairn you saw wasn’t a mirage. You might as well carry a sign that says, ‘I have no idea where the hell I am.’

It’s less about following a path and more about wandering aimlessly through some of the most remote, bear-infested, life-questioning terrain America has to offer.”

Long Trail

“At least when you finally limp into town, there’s maple syrup waiting… if you survive.”

What on earth does GPT think goes on out there?? —Eds.

“The Long Trail: Vermont’s finest attempt at turning a pleasant walk in the woods into a survival challenge. It’s 272 miles of mud, rocks, and roots—basically an obstacle course designed by a sadist with a grudge against ankles. This is the trail for people who think, ‘Hey, I’d love to get Lyme disease and trench foot in the same weekend!’

Think you’re here to enjoy the scenery? Ha! You’ll be too busy trying to stay upright while your boots get swallowed by mud bogs that look suspiciously like portals to another dimension. And when you finally hit a ‘summit,’ congratulations! You’ve earned a stunning view of… fog. So much fog, it feels like the state installed it just to remind you that clear skies are for suckers.

But hey, at least when you finally limp into town, there’s maple syrup waiting… if you survive.”

Arizona Trail

“‘Oh look, another cactus.'”

There is literally absolutely nothing but cacti out there. The Grand Canyon is also a cactus. —Eds.

“Ah yes, the Arizona Trail—a sun-scorched hellscape that exists to remind you why humans invented air conditioning. Why hike in forests when you can bake yourself alive in the desert? It’s 800 miles of sunburn, sand, and a whole lot of ‘Am I hiking or just surviving?’ Imagine staring at endless cacti, knowing they’re better hydrated than you’ll ever be.

The Arizona Trail is perfect for anyone who’s ever looked at the surface of Mars and thought, ‘Yeah, I’d hike there.’ It’s 800 miles of rugged, sun-scorched beauty, which is great if you enjoy the sensation of slowly turning into jerky. The trail offers such diverse scenery as ‘more desert’ and ‘oh look, another cactus.’ Don’t even get me started on the joys of setting up camp in the middle of a dust storm—fun for the whole body!

And can we talk about the Grand Canyon section? Sure, it looks amazing, but it’s really just the earth mocking you, like, “Yeah, go ahead, walk down here … good luck getting back up without a medevac.”

Sure, there are mountains—after you’ve slogged through the desert, you get to climb them too, because Arizona believes in equal-opportunity suffering.”

John Muir Trail

“Yosemite’s greatest hits album, but with more suffering.”

Yikes. The truth hurts. —Eds.

“Ah, the John Muir Trail, where people go to act like they’re starring in their own personal nature documentary but end up looking like a failed REI commercial. Named after John Muir, the guy who thought wandering around the wilderness was a good time before wifi existed—because that’s obviously who you want to take life advice from. ‘Go to the mountains and get their good tidings,’ Muir said. Yeah, sure, John, I’ll also take their hypothermia, dehydration, and that one bear who’s way too interested in my granola bar.

The John Muir Trail is basically Yosemite’s greatest hits album, but with more suffering. Ever wanted to hike for days while carrying a pack that feels heavier than your emotional baggage? This is your chance!”

Colorado Trail

“Freeze-dried regret.”

Sick. Burn. *slow clap* — Eds.

“The Colorado Trail is a great way to spend your vacation — if your idea of fun involves a daily buffet of granola bars and freeze-dried regret. It’s like the universe decided, “Let’s make a scenic treadmill that goes uphill both ways.”

Oh, and don’t worry about company — you’ll have plenty of chipmunks to laugh at you while you attempt to filter water from a stream that’s just a trickle. On the bright side, after a few days, you’ll finally understand why thru-hikers have that special blend of exhaustion and mania in their eyes.

Oh, and the camping — what a treat! Think of it as ‘nature’s Airbnb’—where your bed is the hardest patch of ground you can find, and the views come with complimentary cold wind. Nothing quite like spending the evening doing yoga-level contortions in your sleeping bag trying to find that one non-painful position while wondering if those distant footsteps are from an innocent deer or something much hungrier.

Don’t get me wrong, it’s beautiful, but after a few days, if you’ve seen one majestic peak, you’ve seen them all. Eventually, you’re just like, ‘Cool, another mountain. Wow, more trees. Are we done yet?’ Plus, if you’re one of those over-enthusiastic hikers who thinks it’s a good idea to bike the trail—congratulations, you’ve just signed up for 500 miles of biking-induced butt pain while dodging people who smell like dehydrated jerky.

But hey, at least you get to fall asleep under the stars, assuming you’re not too busy wrestling with a tent zipper that’s about as reliable as your cell service out here.”

Florida Trail

“The landscape offers a stunning variety of … flatness.”

Hey, it said what it said. In other news, AI thinks the phrase “mosquitoes the size of small birds” is the pinnacle of comedy. —Eds.

“The Florida Trail: where ‘hiking’ is just code for slowly becoming soup in the world’s largest, bug-infested crockpot. Forget fresh mountain air; you’ll be lucky to catch a breath that isn’t 90 percent humidity or laced with the scent of decaying swamp muck. This trek is basically a 1,500-mile slog through everything Florida is famous for, minus the fun stuff. 

The landscape offers a stunning variety of… flatness, punctuated only by the occasional pine tree, like a fever dream you can’t escape. Who needs mountains when you can trudge through endless flat, swampy miles, dodging alligators and mosquitoes the size of drones? Sorry, but if I wanted to stare at flat, mosquito-infested landscapes, I’d just visit a used car lot in the Everglades. You’re not seeing ‘majestic wilderness’ — you’re walking through a soggy version of purgatory, where the only thing more relentless than the humidity is the smell of your own regret.

The Florida Trail promises to keep you on your toes—mainly because standing still means becoming a mosquito magnet. And if the heat doesn’t melt you, the humidity will. It’s like hiking in a sauna, except instead of relaxation, you get swamp butt and a healthy dose of regret.”