Calleigh Little taking a break during her cross-country skateboarding trip in Wyoming.

What does it take to skateboard 3,497 miles across the country? For Calleigh Little, pure will, about $4,100 and the good will of strangers did the trick.

Occasionally reaching speeds upward of 50 miles an hour, she wrapped up her 48-day journey last month having crisscrossed the country from Bend, Ore., to Boston. Making the trek for transgender rights and awareness, her coast-to-coast effort was fueled mostly by her own $2,500 with the help of $600 from sponsors and $1,000 in individual donations — all of which went to food and shelter. Averaging 50 miles a day, the intrepid skateboarder covered 60 to 70 miles on better days, and 40 to 50 daily miles when hanging out a bit was more of a priority.

Ranked first in the U.S. for women’s distance skateboarding and third in the world, Little said her skate across America was spurred by a job she hated and a break-up. After six months of working from home as a social media and e-commerce manager for the fitness headband company Gymwrap, Little decided to head east. “It was just really debilitating working from home,” she said.

As friends worried about how weather would affect the trek, Little said she was well-prepared for the cold weather. “It was more the pavement, wind and elevation changes that affected me more than the weather. I didn’t see rain until I got to Chicago and I intermittently saw snow a few times. But snow never really bothered me,” Little said.

The social aspects took more of a toll. “Having to introduce myself and form relationships with new people over and over and over and over on a daily basis in order to just get basic needs, that became a task for me. It was, ‘Hi, I’m Calleigh. I’m skateboarding across the country. I’m transgender and yada, yada, ya.’ Going through that day in and day out really did wear me down,” she said.

On what she described as the “Michael Phelps Diet,” Little consumed 5,000 to 10,000 calories daily. Finishing her journey 13 pounds heavier — mostly due to muscle mass in her legs — Little said she ditched all of her cooking gear in week one, counting on strangers and barebones diners for sustenance. The most memorable meal was found on a rare rest day in Shoshone, Idaho — the “Hog” a bun stuffed with ham, bacon, bison and a chicken patty atop a salad.

Unlike Phelps, who has an endorsement deal with Under Armour, Little had to buy the base layer top she wore day-in and day-out. Her outfit of choice never changed — REI waterproof pants over thermal leggings, the Under Armour base layer, a wool layer, a cotton shirt and a fleece jacket. Little sought out apparel sponsors but to no avail. “I got a lot of ‘no’s’ because I planned the trip pretty hastily. I decided I was going to do it and then left a month later,” Little said.

For competitive purposes, she has an apparel sponsorship with Cindy Whitehead’s Girl Is Not a Four Letter Word. They are working on Little’s book and modeling for the brand. “Her clothes are for women, but everything she sells is one-size-fits-all. In terms of my body and the average woman’s body and the non-average woman’s body, I’m sort of perfectly in the middle to be modeling those types of things.”

With a pretty well-rounded repertoire of sponsors — Original Skateboards and Riptide Sports among them — Little didn’t pick up any new ones. In a few weeks, she will be competing for the women’s world record for the 24 Hour Miami Ultraskate. “With all of my skateboard sponsors, this is kind of the final rite of passage to finish everything up. I conquered the country, now I’ve got to conquer the world with a record,” she said. (Little is trying to cap off the race by skateboarding Florida from south to north.)

The beauty of Wyoming’s mountains, rivers, trails and canyon was unlike any other state. Just across the Idaho line into Wyoming, a passing cyclist told Little, “‘If you go through any stretches of uphill, when you get to the top, turn around.’ Every time I did, I had views of snow-capped mountains from 8,500 feet up. There aren’t enough words to summarize it.

“My favorite part was definitely camping. Every single time I laid down in my tent — wherever I was — I was able to let out a long deep breath and just say, ‘I don’t have to be around anybody. I don’t have to ask anybody anything or rely on anybody.’ Most of the time camping I had no phone service because I was in the middle of nowhere. It was just an unreal experience.”

Having only been back for a month, Little “is still trying to get a grip on reality and things like that.” In the meantime, the trip’s finer peaks remain. “No matter what state I was in, there was always a kind soul who stopped on the side of the road to ask if I needed help, or a ride, or a place to sleep. Diners often comped my meals in exchange for a business card,” she said. “We often get our perspective of people based on how the demographic votes, or how the people are portrayed through social media. My experience was the exact opposite of what I was told to expect. People are surprised to hear that I didn’t carry any sort of self-defense weapon and often jumped in stranger’s cars or stayed in stranger’s homes. I never felt unsafe, whether camping on the side of the road or staying indoors. Even as a trans woman, the kindness and acceptance and welcoming never ceased.”

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