Calleigh Little is doing something quite incredible in the world of skateboarding. She is going across the USA via longboard solo. We caught up with her in Wyoming. Before we get into the interview, here are some of Calleigh’s impressive contest results:

Adrenalina 2016 – 2nd Place Women’s
215 miles – Miami Ultraskate 2017 (Second Place Women’s)
188 miles – Chief Ladiga Sk8 Challenge (Second Place Women’s)
Central Mass Skate Festival 8 – Women’s First Place

 Somewhere in Nebraska



Why do you find long distance and downhill skateboarding so enjoyable?

It’s not so much that I find long distance or downhill enjoyable- I truly feel like both disciplines ask things of me I dont normally do. They enable me to extend myself in ways I never would in any other part of life. Long distance requires a mental focus, extensive planning, and full body commitment. I find that when I am in a situation where my entire being is used, I have an opportunity to see how far I can take it. And then I take it further.

Downhill, on the other hand, is a streamline of panic, fear, focus, and commitment. I absolutely adore the moments where I have no idea whats coming up after a turn. How will I react? Do I fully tuck or do I have to prepare for a predrift? When I’m going fast, no other questions matter. I dont worry about student loan bills. Who cares what that guy said to me last night? All that matters is that I make it down safely. I love that.

What made you decide to go solo across the USA?

When I first came out as a transgender woman, the world hadn’t even begun to bring it into the mainstream news. I didn’t have all kinds of acceptance, and I certainly didn’t have the friends I do now. That was 3 years ago. The world wants to make it seem like it’s being shoved down their throats, but its just a new thing the media is okay with talking about.

Now, three years later, I didn’t want to run away from anything. I had friends all over the globe from competing. I wanted to do it solo for me. I came to a point where I wasnt learning anything anymore from the people I interacted with. I knew there had to be more to learn. If I did it with someone else, the experience could have been about our experience together, and not my experience with the world.

Where do you think your competitive spirit comes from?

After a long life of being beaten down and coming up short, I found that my competitive edge was a product of me wanting to rise above. People tend to think that I have always been on top- its simply not the case. I experienced enough life to a point where I had to fight back, I had to be myself, and I had to win. I have been so sick and tired of sitting in the back of the class. I trained and fought and trained a bit more. And when I sat down at the end of the day, I thought about training again.

What has been your best experience so far within skateboarding?

I think the best experience within skateboarding has been the vast amount of friends I made. Every event I attend has people I look forward to meeting, whether it is downhill or long distance. I learned of a world where people encouraged me and pushed me, and made me work for everything I had.

If I had to narrow it down to just one experience, my absolute favorite was winning the Central Mass 8 women’s division. It was a race I attended for years, and I picked up everything I could to figure out how to win it. It was neck and neck all the way to the end and a true photo finish. My friends dumped champagne on me at the podium and for once in my skate life I had earned my title.

What has been the worst experience and how did you deal with it?

Worst experience…they are few and far between. The world is a good place. The absolute worst, though, was when I had just kicked off for the 24 hour Ultraskate in 2017. My biggest competitor had turned around and said, “If you’re going to race as a woman, you need to pee like a woman.” I could have taken it a million ways. I could have dwelled on it for 24 consecutive hours of skating around in a circle. I could have quit. Instead, I appeased the proposal- given that I only urinated once in 24 hours anyways, I retired to the bathroom and peed. The guys usually just drop their shorts and pee as they skate. I did go on to lose to her by only 10 miles that year, but it burned a fire in me to fight harder.

Adrenalina Marathon

You mentioned at the Longboard Girls Crew website you are lost between jobs and are questioning the meaning of everything. The fact that some stole your intellectual property must have been devastating. Is this trip helping you deal with that loss?

It totally hurt that the company I was working for used me for my creative work, forced me out, and then didn’t pay me. Legally I have all of the rights to everything I created as an independent contractor without a signed contract. I didnt have the means to hire a lawyer. I was flat broke. I began selling my collection of boards and gear to make end’s meat and often went days without eating. It hurt a lot.

I learned, once again, to fight back. Even if I did sue for my rightful property it could have been years of litigation. I wasnt going to see a dime that could have helped me at that moment. I looked for a new career for two months, struggling along, doing 2 or 3 interviews a day and ended up with a job at a burger place. I knew I was worth more than a job at a burger place, so I formulated my plans to follow my dreams. I could only struggle for so long.  I sold my motorcycle, stopped paying rent, threw away everything I couldn’t sell, and fit my life in a backpack. With the help of my friends, the companies who support me, and the money I earned from selling my belongings, my dream didnt seem so far off. So I made it happen. No longer was I going to slave away at a job I hated putting money in someone else’s pocket. I realized this life is mine and it is what I make it.

What do you plan to do once this feat is accomplished?

Honestly, I have no idea. I’d love to expand on my blogs and sell them as a book. I’d also love to turn around and go back the other way. Mostly, I plan to take my experience and use it to be the number 1 female distance skater in the ultraskate. As for where I’ll live or what ill do for money, who knows? I still have a tent and a skateboard- the world is my oyster.


Harsh question to ask – but I would like to ask what do you say to people who feel this whole “transgender thing” is all about seeking attention? Instead of seeing your bravery, they just question your entire reason.

Haha. I get these comments all the time. It’s hard for me to take them seriously. Its not about being transgender, and it certainly isn’t for attention. I planned and left for this ride in a month’s time. I’ve been trans for as long as I can remember. I race with the girls as any other girl would. There was an article written about me on Gay Star News that wanted to highlight my identity as a transgender woman because of the relevance to their audience and people saw it as a big slap in the face, like I purposefully slathered my identity around. Trust me, if I could be seen and accepted as any other girl is, I would kill for the chance.

But I think the use of telling people of my transgender identity is more for other trans people in the world. I want them to know I am trans. I want them to see that we dont have to hide in our bedrooms. We can go to the corner store as ourselves and we can be a part of society. As I skate I see all different kinds of people, and the grand majority have accepted me and spoken of my bravery. I think it gets a little twisted when you read it in an article versus witnessing it in real life.

Imagine seeing someone skateboarding past your house with a 30 lb expedition backpack and saying, “You just want attention!” Its a little ridiculous. At the end of the day, I’m out here making my dreams come true, tethered to nothing, while others somehow find a reason to feel taller than me. I’ve never felt taller for making someone else feel small.

What’s been the reaction from the various articles you’ve had written about you?

I spoke about this in the last question a bit, but its really a mixed bag. I can with 100% certainty say that it has been all straight white men who have a problem with me. I am a woman, I have lived as a woman, I have endured the horrible society women live in every day, and their opinions don’t change that. Whether they want to fall back on some pseudo-scientific argument to denounce my gender or just speak out of bigotry, it doesn’t change anything. I have never sought respect from anyone who didn’t have mine.

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