This past Sunday, a handful of people gathered at the Boston Marathon finish line and cast their eyes down Boylston Street looking for her. Each time we’d hear a skateboard on the pavement, our attention would be snapped back to the street. And then finally she appeared, weaving her way past parked cars. Trans woman Calleigh Little raised her arms in victory and punched the air. The enormity of her finish was of little consequence to the strangers passing by.

Before she got started on her trip, Little, whose inflection over the phone is a subtle mix of Boston earthiness and relaxed Southern California, was confident. She has several years of long distance skateboarding under her belt throughout New England and Southern California, as well as professional Long Distance Pushing races along both coasts. “I’m not nervous, I’m ready,” she said.

Only two other people, both cis men, have ever successfully skated across the U.S. solo. The trip itself is a grueling test of endurance, planning, and resourcefulness. Managing a food supply that provides enough energy for a body to skate a hundred miles or more every day for a month and a half is a nearly impossible task in unfamiliar geography and sleeping in a tent is not as simple as it seems.

For trans women, the athletic experience is often one of controversy. For decades, they have suffered through accusations that they have an unfair advantage due to being assigned male at birth, and ensuing witch hunts that involve cruel sex testing. Despite very little evidence that trans women have a significant advantage over their cis counterparts, sports pages tackle the issue with very little nuance or understanding of hormonal science. It’s hard to find a sports story featuring a trans woman being celebrated. Enter professional long distance skateboarder Calleigh Little.

“I just skated from Oregon to MOTHERFUCKING BOSTON!!” She screamed as she spiked her board in the middle of the street and collapsed in an exhausted heap.

Little took up long distance skateboarding shortly after her transition in 2014 as a way to get to work and around town because she lost her driver’s license and couldn't even afford a bike*.** LDP as a sport was born out of illegal street races like the Broadway Bomb\, a spectacle involving hundreds of skateboarders bombing through the streets of New York, weaving in and out of traffic and through crowds of pedestrians before finishing at the Brooklyn Bridge. The sport has grown quickly over last decade and while once there was an edgy, almost illegal vibe, LDP has formalized of late, complete with a governing body , media coverage, and multiple professional events across the country. As a pro, Little doesn’t make any money on LDP—but she does have sponsors who provide gear. She’s ranked the no. 1 woman in the United States, and no. 3 in the world.

But when asked what she feared most, she said it was mother nature itself as she set out from Oregon in mid October. “The weather definitely makes me nervous but I went out and got four season gear, winter jackets, gloves. I’m pretty much ready but nobody likes being cold. Coming from living in Southern California to being up here in the Pacific Northwest, I forgot what cold is.”

“As I was walking up this steep hill, a car pulled up and the driver was like ‘You look like you need a ride.’ At first I didn’t want to because I was going for this record but the guy persisted. ‘No really, you’re going to want a ride, there’s a snow storm up ahead.’”

After careful route planning involving the latest mapping technology to measure everything from the grade of each road to the quality of the pavement, Little decided to start heading east from Bend, Oregon after completing the 5k/10k and 25k races at the Bend Beatdown, a popular annual LDP event. She initially intended to treat her trip like a race and loaded up her pack with food, cooking gear, and loads of clothes, an indication that she didn’t plan on making a lot of stops along the way. In her mind, she was chasing the calendar to make it across the country faster than anyone else on a skateboard ever had. As she struggled through the terrain of eastern Oregon, however, a snowstorm almost immediately derailed her plans for any records.

Additionally, Little hoped to bring awareness of trans people to areas of the country where they are not as typically present. But what started as a chase for the history books, turned into a valuable lesson on the humanity of strangers.

Little initially set out to prove that gender doesn’t matter when it comes to speed and endurance on a skateboard. “I’ve been racing with women for a few years now and I get a little backlash [for being trans] but I’m just blown away because I’ve seen women break the world speed record on a skateboard and in distance too I’ve seen cis women just absolutely blowing me away with the times they’re getting. I just want to prove that gender is insignificant and it’s about how much you want it. I’m doing it for all women.”

She acquiesced, throwing her 55 lb backpack in the backseat to catch a ride to the next town. At the time, she reasoned, she was simply trying to survive. She was determined to get to Boston by any means necessary. It would not be her only ride from a stranger, she estimates that she covered about half of her mileage catching rides from strangers. A decision that comes with a tremendous amount of risk for a trans woman.

Hitching too many rides would risk any official records but to Little, the thought of walking through a storm held little appeal. And it was not like she’d be able to break any records skating through the snow anyway.

She hit one snag in Boise, Idaho where the roads were much rougher than expected as winter neared. “They had beautiful pavement down there, which is what I had heard, but by the time I got there, they had chip sealed everything. So riding over it was complete hell and I was screaming and crying. Think about skateboarding over loose rocks, it was awful.”

Little slept outside a lot, especially early on out west, which meant tying up her food in a tree away from her tent, in case a hungry bear came along. The reality of sleeping in a tent all night while also spending long days on her board meant that Little was constantly battling the elements.

Eventually, Little abandoned many of her supplies, dumping most of her clothes, food, and cooking gear along the side of the road with a “free” sign attached. The lightened load helped make her days on the board more manageable but abandoning her food meant she needed to skate from town to town and city to city for food and shelter. She frequently went without both.

I just want to prove that gender is insignificant and it’s about how much you want it.

Using a combination of warmshowers.com, a site cyclists use to find a roof to stay under on long distance rides, and Tinder, Little managed to avoid sleeping outside most nights. And in the process, met hundreds of everyday Americans along the way, many of whom had never met a trans woman before. “I can’t tell you how many times I walked into a random bar out west and I was the only person not wearing camouflage.” This often led to interesting situations when Little had to use the restroom.