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Boston native skates across country for trans rights and awareness

On a Sunday earlier this month, Calleigh Little was making her way down Boylston Street toward the Marathon finish line, weaving her way through pedestrians and parked cars. To those who noticed her, she looked like any other skateboarder; apart from the huge pack on her back, there was no way of knowing that once she crossed that finish line, she had completed a rarely attempted quest.

Little raised her arms and screamed as she finished, and the handful of acquaintances gathered let out a cheer.

“I just skated from Oregon to MOTHERFUCKING BOSTON!” Little yelled as she spiked her board and collapsed on the cold pavement.

Only two other people, both cisgender men, have ever successfully skateboarded across the country solo before. It’s a tremendous test of an endurance that requires meticulous planning and survival skills. With her signature winged eyeliner and a 55-pound pack on her back, Little became the first woman to attempt it, though she got plenty of help along the way from friends as well as strangers.



Little is a 26-year-old Boston native who’s been living in San Diego. She’s also a professional in Long Distance Pushing, a sport born out of illegal skateboarding races like the Broadway Bomb, an intense underground weave through Manhattan. While Little doesn’t make any money from being a professional, she does have sponsorships from companies within the LDP scene.

The trip was an incredible exposure to parts of the US she had never seen. “I hadn’t really left the coasts before,” Little told DigBoston in an interview. She battled extreme weather, hitting snow in Oregon, Idaho, and Ohio, as well as rough roads, scarce food and water, and illness. But there was another challenge that Little had to manage as well: She’s transgender.

Transgender rights are a hot-button political issue these days. Controversies ensued in early 2015 in the wake of a repeal of the city of Houston’s LGTBQ nondiscrimination ordinance, which was defeated by a campaign with the tagline “no men in women’s bathrooms.” A few months later, North Carolina passed its now infamous HB2 bathroom law, forcing trans people to use the bathroom consistent with their birth certificate.

Last year, here in Massachusetts, Gov. Charlie Baker signed into law a bill that protects trans people in public accommodations, so trans people can now use the bathroom or changing room consistent with their gender identity without harassment. Despite that progress made to protect trans rights in the legislature, Mass Resistance, a national anti-LGBTQ group based in Waltham, has organized opposition and gathered enough signatures for a referendum to repeal the new law in 2018. It will be the first time that trans accommodations rights on their own will be voted on, an important test for the future of trans rights nationwide. If trans rights fail here, they could be voted down anywhere else in the country. Enter Calleigh Little’s cross-country skate.

Little herself admits that she’s not very political—not because she doesn’t have opinions, but because she doesn’t always feel the need to express them. She finds it hard to believe that Commonwealth voters would take away valuable trans protections.

“C’mon, it’s Massachusetts,” she said in a post-finish interview with DigBoston at the Pour House on Boylston Street. “I don’t think the people of Massachusetts would do something like that.” Nevertheless, one of the reasons she set out from Bend, Oregon, was to raise awareness of trans people and their issues in parts of the country where folks might not have 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,” Little said.

Along the way, she had to manage her bathroom use for safety reasons. While none of the 15 states she skated through explicitly ban trans women from women’s restrooms, only Illinois and the coastal states she passed through offer protections from bathroom discrimination for trans people.



Little noted at the finish line that she only had to shit in the woods once, an especially impressive feat for a trans woman who battled the effects of parasites from drinking out of a river in Wyoming, plus endured diarrhea and vomiting in Nebraska, Iowa, and Illinois. When asked about how she determined the safest potty option, she explained that she just played it with care, especially out west. Because of the weather, Little said she often rolled into towns with her face covered and a winter hat over her long, strawberry blonde hair. With her body and face covered, she said it was often easiest to just walk into a place and use the men’s room without risking confrontation.

It was the people, however, that Little met along the way that she won’t ever forget. “I feel like I have homes in 15 states now,” she said. As we spoke on Boylston Street, she told stories about people she met along the way. “I found my life on the road,” Little said.

At times on her journey, she recalled that strangers often dropped everything to help her along, or to buy her food and tons of coffee, with none of them caring that she was trans. “Gender isn’t important when you’re out in the middle of nowhere, gender isn’t important when you’re running out of water in the middle of fucking Wyoming, none of it really matters. The only thing that matters is the connections you make and the people you make them with.”

And when that coffee ran through her body, she simply wanted to use the restroom in peace without harassment.

Learn more about Little’s journey at

This article was produced by the Boston Institute for Nonprofit Journalism and published in DigBoston.

Katelyn Burns is a trans woman and freelance journalist based in Maine. Her previous work has appeared in many major publications including The Washington Post, VICE, and Rewire.

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