In Florida, America’s flattest state, this man climbs to the highest points

ST. PETERSBURG — So there’s this guy.

He’s a colleague of a friend who comes up in casual conversation.

The guy, says friend, is kind of quirky.

He plays French horn for The Florida Orchestra. That’s his job, but it’s not the quirky thing.

The guy grew up in Boston, went to music school in Philadelphia and later took jobs in Miami and Shanghai and Colorado and Tampa.

Colorado is where the story begins.

The guy — “really nice guy” — was working a summer music festival there and started to get into hiking. It’s Colorado. What else do you do?

He climbed with friends, scaled these big impressive peaks with views that make you want to believe in a higher power or shore up your belief if you already do.

Then, one day, he turned the climbing into a game.

He began a quest to visit the highest point in every county, to work his way through the state.

In Colorado that often meant big climbs on trails with magnificent views.

But now he lives in Florida — the flattest state in the country — and he’s doing the same.

The high points are in orange groves. Random roads inside gated communities. The parking lot of a mall with a Cheesecake Factory.

This is how he spends his free time. Poking around patches of concrete and swamp. Driving hundreds of miles to stand in the middle of a cow pasture, a cemetery, a stranger’s backyard.

At least that’s what you’re told.

You have to meet this guy.

You have to.

Sometime in May, 2023

You’re standing in line for a drink at a local brewery when you’re introduced.

“This is the high point guy,” your friend says.

He’s got a newsboy cap, boxy glasses, a graying goatee.

He looks surprised, skeptical even, when you tell him you want to know everything.

Then he lights up like he’s been waiting for someone to ask.

Andrew Karr

The high point guy is Andrew Karr and he lives in an old South Tampa apartment that gets really great morning light.

It’s a modest but comfortable place — a one-bedroom with space for a music stand and a desk with a paint-by-numbers poster that’s been in progress since early in the pandemic.

Andrew is 46. Single. He’s been doing this highpointing thing for the past 10 years.

Highpointing, as it turns out, has a culture of its own.

There’s a community of people, mostly connected by a website maintained by a Microsoft engineer in Washington state, who task themselves with visiting high points across the country and world. Unlike mountaineers, they’re less driven by spectacular views or the challenge of an uphill climb. It’s the pursuit that pulls them in.

Sure, they’re often athletes — certainly outdoorsy types (OK, mostly men) — but more than that, they are nerds. People who love puzzles and journeys and problem solving. The act of standing on various pieces of Earth just because they can.

There are message boards, where people debate who really completed a climb. Yes, you visited the highest contour, but did you stand on this specific line?

And one need only look to the Hall of Fame on Peakbagger.com to see that there’s a history, too.

The first on the notables list? Sir Hugh Munro. He climbed a series of peaks around Scotland in 1891.

Some 122 years later, Andrew was browsing a Boulder bookstore, and happened upon a how-to guide for county highpoints out west.

That it piqued his curiosity makes sense. He’s a geography fanatic — the winner of his 8th grade geography bee!

He’s always loved road maps, studying their lines and how they connect — though he didn’t learn to drive until he was 30. There’s just something about the way maps make the world more knowable that brings him delight.

His life has its fair share of chaos — a chore chart stuck in March, stories from friends about how he said yes to meeting up at the Eiffel Tower at 3 p.m. on some faraway date — but mixed with disorder and spontaneity are lethal doses of fixation.

Obsession is what makes him a master of a particularly finicky instrument.

And it’s what’s kept him hooked on highpointing for a decade.

Before each trip, Andrew researches the land, its history, the town. He figures out whether it’s accessible by trail or if he’ll have to go off-roading. He fills a lined notebook with comforting coordinates and travel times in tiny strokes of pencil.

The spiel

Andrew has complicated rules. He keeps lists of hopeful expeditions, like an ever-expanding board game.

There are subquests, like the Adams counties of America — he’s completed all 12, from Idaho to Pennsylvania — and peaks along highways and byways.

In Florida, he’s working through the counties in alphabetical order.

He’s been to the high point in 61 of 67 so far.

The highest point in Pinellas County?

It’s a tie between a spot on the Countryside Golf Course and one near the parking lot of the Countryside Mall. He’s been to both.

In Hillsborough County, the highest point lies in scrub just beyond Alafia River State Park. Done.

Peaks in other counties have posed more complications.

Reaching them has required renting kayaks, or chartering private ferries. Andrew has ridden bikes deep into forest trails. He’s knocked on doors in Florida backcountry, bearing Publix cookies, to ask permission to traverse private ranch land, or to stand on somebody’s lawn.

He has a spiel rehearsed like a door-to-door salesman: “I know this is crazy, but I go to the highest places in counties, and your back field or yard or driveway happens to be the highest point here. I would love to visit and say that I stood on the Mount Everest of Pasco County, Florida.”

That’s always the one that gets them: “The Mount Everest” of wherever he is.

There’s a good amount of privilege, he recognizes, to feeling safe on these expeditions. He’s white. He doesn’t offer up that he’s a Jew or a gay man. Sometimes, when there’s no one around to grant permission, he’ll trespass.

But he has rules for breaking rules: He won’t venture beside houses or structures or on land with people’s livestock without their blessing.

“Only minor trespassing,” he says.

Up next is Taylor County, but he’s reached a bit of a stalling point.

The highest point sits in a massive patch of woodland owned by a billionaire.

He’d have to trek 14 miles through private land.

He’s working on it.

The Quest

Andrew Karr agrees to let you join a quest. Not the one to Taylor County — “they might get spooked,” he says — but to one of the other hills on one of his other lists that’s in a state forest north of Orlando.

You drive there in his lime green Subaru, listening to a mix of symphonies and language lessons. Andrew speaks 12 languages, most conversationally, though he wouldn’t tell you he’s proficient in anything but English. In the car, he practices Ojibwe. Then Mandarin. Then German, then French.

“Kind of a genius,” a friend of his said.

After he parks, he pulls a hiking pack from the back of the car, where a rain slick and a paper map lie against a black suit. His two lives.

You ask Andrew what he does when he’s not playing the French horn or planning these quests.

“What else is there time for?” he quips.

“It’s a hobby for single or retired people,” he admits.

For years, Andrew struggled to find stable employment. He attended the most selective music school in the country but ended up working as a Starbucks barista between orchestra jobs. He’s moved a lot, played a lot of poorly paid gigs. Struggled with workplace dynamics — mostly competition. At one point, he considered leaving music to become a pilot. He thought it would be something that would help with his hobby.

He took flight lessons, but that flame went out. Now, he’s happy in his job again but always ready for the floor to fall out from under him. That’s how musicians are, he says.

Does highpointing give him a sense of control?

“No,” he says, and pauses. “No, that’s not it.”

The path you head off on is wide and sandy, lined by scrub and palm and skinny pine trees.

It’s a little after noon, and summer is approaching but it’s overcast, thank God.

For 40 minutes you walk in a straight line. One foot in front of the other. There’s a decomposing snake just past mile one. A flattened frog a little farther.

Around mile three the path begins to curve. You cross a river that runs north to Jacksonville, and Andrew tells you about the logging industry that used to rule this land, and how the water was used to transport goods. Then, he takes out his phone and checks his map.

In a satellite image, you see the land you’re traversing.

There’s a blue dot (that’s you!), and a red dot a few hundred feet away that marks the highest point for miles. That’s the peak.

The “peak.”

Getting there requires off-roading, so Andrew takes a sharp left from the trail and plunges into the uncharted woods. Spread-out pines and palmetto quickly turn into a thicket of bramble, but Andrew uses a satellite image to try and steer toward the clearest path.

He pushes through branches, stumbles over roots, takes a spider web to the face.

A thorn catches on his hiking pants. He’s ruined a lot of clothes this way.

The dots on the map get closer with every step and stumble. Then, about 10 minutes later, they’re touching.

Andrew crouches and shields his face with his arms, pushing through a final wall of vegetation, his dark hair disappearing into the scrub.

“I think this is it,” he says.

He scans the area just to be sure. There’s a self-aware nonchalance, but he can’t mask the satisfaction.

“We made it. Look at the view!” he gestures.

You look around. It’s flat. You’re standing in a bush.

Lay bare your damage!

Everybody wants to know why you’re writing this article.

Andrew’s colleagues.

Andrew’s friends.

Andrew’s dad.

“So it’s just, like, a story about the fact that he does this...?” one unnamed interviewee inquired.

While Andrew plows ahead, crossing off coordinates, you’ve embarked on an aimless search of your own.

Why? Really though — Why, Andrew, would anybody spend their time like this?

At a newsroom meeting, a colleague puts it more bluntly: “What’s this guy’s damage?”

Through a month of back-and-forth conversations, you go to lengths to find out.

But your efforts turn up little dirt.

Andrew tries gamely to answer your increasingly desperate queries.

The hobby has brought him to patches of America he wouldn’t have otherwise seen, he explains, where cultural and political beliefs vary drastically from those in the town he grew up in.

He’s gotten to visit mom-and-pop restaurants with over-the-top cakes and pastries. Coffee shops in rural towns, run by queer people.

He’s watched Florida’s landscape change. Highways have emerged where forests stood. Hurricanes have decimated communities, carving away Panhandle pines. Fields of condos have bloomed. This place, which has not always felt like home, he’s come to know from the inside out.

Still, he says, all that is secondary.

You might not understand, not fully. But as you listen to him, and explain the story you’re writing to yet another person who asks, you finally see it.

Here is a person doing something for the heck of it. Because he thinks it’s fun. And he likes it. And it isn’t hurting anybody. And it makes him feel happy.

Since speaking with the Times for this story, Andrew has climbed an additional 35 peaks, ranging from Florida state park high points to “real mountain hikes” in Vermont and New Hampshire. He’s currently working his way back to Colorado for a summer music festival, where his highpointing journey began. Andrew plans to return to the Sunshine State at the end of summer, when he’ll resume efforts to cross Taylor County off his list.

To learn more about highpointing and join the community, create a free account at Peakbagger.com.