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Meet the First Trans Woman to Travel Across the US on Skateboard

2018 Miami Ultra Skate Champion Calleigh Little on the lack of women in skateboarding, struggling with her gender identity, and opening up in her new book.
Photo by Anne Rearick/Agence VU

Calleigh Little is the 2017 International Distance Skateboarding Association champion in her class; she also placed first in the women’s longboard 25-kilometer Bend Beatdown in 2017, and the Miami Ultra-Skate in 2018. As the first woman and first transgender athlete to complete a cross-country solo skate, she’s blazing trails both for trans athletes and for the sport of long-distance skateboarding, also known as long-distance pushing.


Her high-profile feats are helping bring long-distance skating into the mainstream, and keeping Little at the forefront of the sport. These days she’s also busy raising awareness about trans issues in hopes that sharing her triumphs and struggles will inspire others like her. Although she’s mostly known for breaking records in the skateboarding industry, Little also works as a freelance brand designer and marketer. But above all, she considers herself a writer. She’s chronicled what it’s like to travel across the country as a trans woman, sharing her experiences with friends, family, and fans via her blog and Facebook page. Those writings have become the basis for Little’s forthcoming book, Carrion, Carried On.

Photo courtesy of Calleigh Little.

We asked Little about the challenges of long-distance pushing, accomplishing goals, and fighting to be recognized and respected in a male-dominated subculture.

This interview has been edited and condensed for clarity.

On finding serenity in skateboarding
I was kind of always a skateboarder, and I was always looking for different kinds of boards to use. I was always the kid running around with a 5" wide deck when everyone else rocked their narrow 7" ones on the stair sets, and I was the first to take a shot at longboarding out of all of my friends. I found a lot of serenity in taking the board on a lengthy cruise or [at] high speeds down hills. Eventually, it all clicked when skateboarding became a necessity for me to use as transportation, and from there, the rest is history.


On claiming and owning space
My favorite thing about being a skater is being able to make that term my own. Skateboarding is so dynamic, whether you're doing downhill, street, vert, slalom, or long distance. They’re under the same umbrella term of "skateboarding," but can be almost entirely different. I take a lot of pride in owning "long-distance skateboarder," and a lot of that comes from being at the forefront of bringing it to mainstream audiences. My least favorite thing about skateboarding is the lack of female representation, participation, and competition. It's been steadily growing over the years but, in general, I’d love to see more women on boards.

On going the distance
The challenge is definitely the most attractive thing about travelling distances on human power alone. I never found myself challenged in work environments, and even graduating college was more something I did, and not something I worked at. All of my adventures feel like 100% of me is required: physically, mentally, and emotionally. It's hard to escape that feeling; I wonder why I ever stop sometimes. Plus, being out on the road is this amazing experience where my gender identity isn't such a topic to the people I meet. Regardless of their politics, [on the road] everyone seems to see my accomplishments instead of "sexual deviancy."

Photo by Anne Rearick/Agence VU

On the Chief Ladiga Skate Challenge (a 3-day, 188-mile race she completed this May)
That race is, by far, the most grueling challenge we have in our lives as long-distance skateboarders. However, since I had [already ridden] 900+ miles from North Dakota to get to that race in Georgia, I was very physically prepared compared to previous years. The toughest part this year was setting a last-minute goal to try and break the women's speed record for all three days, and staring down the barrel of a stretched hamstring injury on the final stretch. I missed the mark by only a few minutes, but I was thankful to come out without any pain. Through it all, I couldn't have done it without Spencer Steelman, a fellow adventurer who joined me on my 400-mile, six-day adventure from Miami, Florida to Jacksonville, Florida. Without his encouragement, I might not have found the merit in getting into the Top 10 finishers like we did.


On her passion for writing
I've always been a writer, for as long as I've been a marketing professional, a web designer, and a skateboarder. I consider myself a writer before all, and many of my life goals include well-produced finished works of my writing. Often I'll find it so much more meaningful to be told that someone reads my blogs or my work and likes it more than being congratulated on a skateboarding win. Sharing myself, in my rawest and most honest form, is important to me; I get sick of seeing these Instagram adventurers using marketing phrases and trying to sell themselves without doing anything actually challenging (to me at least). I want to be the anti-version of that. Raw, true, honest, and compelling stories of what it takes to give it your all to achieve a dream—I want people to find that inspiration through me.

On her new book Carrion, Carried On
The book is a chronicle of my skateboarding adventures through hilarious pictures of roadkill I found along the way, with intense tales [included] as excerpts. It's really the ultimate look back at what it took to make it as far as I did and I'm so amped to be able to share it with fans and friends alike. I launched it on Kickstarter as a self-published photobook on July 20 with a small goal to get a first batch out, and will be selling future copies on my website.

On how skating across the US changed her life
I can think of two times specifically where I was at my worst: before I started skating across the US, and after I skated across the US. Before, I was down on my luck with career goals and financials, love, and [my] social life, with a hint of issues with drinking. After, I was down on my luck with health issues, loneliness, and a somber reflection on what I gave up to achieve [my] dream. Both times I found that the act of swallowing it all down and fighting for a new achievement made it easier to handle. Being on the road made me forget lost love and a stack of debt. Winning the 2018 Ultraskate made me remember what I did have, instead of focusing on what I gave up.

"I spent so long telling myself, 'Once I accomplish this, this, this, and this, I'll finally come out.' Don't do that. Make it your priority."

On struggling with gender identity
I spent so long telling myself, "Once I accomplish this, this, this, and this, I'll finally come out." Don't do that. Make it your priority. Your health, your happiness, and your life will all increase greatly if you put your identity first. I know there are things in the way and there are obstacles to overcome, but facing them head on will be something you can look back on with a sense of pride, instead of a sense of regret. Be you, be proud, and be loud. There is no time like the present.

On the excitement that comes with change
My life is totally different than it was a year ago. I found love, I built a small business, I wrote a book, I bicycled across the country, I won the ultimate long-distance skateboarding race, and I created a whole new set of goals and dreams for me to accomplish. It's been a crazy ride from being depressed and alone to feeling like I actually have a say in how my life turns out. But the thing I'm most proud of is being able to admit that I'm happy with who I am, and excited for many more years to come.

25 Strong is a new series highlighting people who have broken barriers and changed culture in 2018. Created with Reebok.