October 10, 2017 at 4:59 pm

Calleigh Little's made a name downhill, including taking first place in the Central Mass Downhill Ladies category. What tends to be the most talked about aspect, for better or for worse, is the fact that Calleigh is a trans athlete. Frankly, we do not care how she wants to identify, just the fact that as a skater she breaks the barriers and does so with style and grace. And in her own way, she is now walking across America in skateboarding and is seeking your awareness and support as she pursues her goals. Support his journey here.

From Calleigh:

Hi. On October 9, 2017, I will embark on a cross-country skateboarding trip from Bend, Boston, MA. This video is a short introduction on what it means for me to complete the ride, the inspiration, and a short on me. Thanks to Original Skateboards, Orangatang Wheels and newton Trucks for their continued support in my efforts. Nothing but the best under my feet from west to east. Support his journey here.

Discover his installation:

Here is a little more of Calleigh's Fundraiser page:

I'm calling Calleigh Little. I am a 26 year old transsexual woman from Boston, Massachusetts. I skateboard for over 6 years and compete for 2.

Personal Records:
64 miles – Milford, MA to Boston, MA and back
71.1 miles – Southborough, MA to Manchester, CT
70.8 miles – Southborough, MA to Hampton Beach, NH
82.4 miles – Framingham, MA to Providence, RI and back
172 miles – Miami Ultraskate 2016 (second place in women)
188 miles – Chief Ladiga Sk8 Challenge (first place in women)
138 miles – Boston, MA to Provincetown, MA
100 miles – Milford, MA to Satan's Kingdom, VT
Bend Beatdown – 5k 3rd place women / 10k 2nd place women
Adrenalina 2016 – 2nd place women
215 miles – Miami Ultraskate 2017 (Second place in women)
188 miles – Chief Ladiga Sk8 Challenge (Second place in women)
Central Festival of Skate Mass 8 – First place women

On October 9, 2017, I will embark on the greatest journey of my life. Departing from Bend, Oregon, after a 5km, 10km and 50km race, I will head east to cross the United States of America skateboarding. I have been planning this trip for 3 years and have made great progress in my skateboarding career to make it a reality.


Competition in women's sports has been an incredible experience for me. I've learned a lot about what it means to be transgendered over the years to surpass myself. I've experienced being the only transgender runner in remote skateboarding, and I hope to set the stage so that others like me can be confident of being their true self in a world that accepted. I can only hope that my determination to pursue my dreams will inspire others to do the same.

At the end of this trip, I will land the following world records:

– First transgender person to cross the United States by gravity
-First woman to skateboard across the country
-More known skateboarding Across the United States

This trip is totally unsupported – there is no car following me, no shelter provided, and only my will drives me to complete it.

Your gift to this cause will go a long way. In addition to affording you access to necessary survival tools like food, water and shelter, a percentage of your donation will be donated to Water.org – a charitable organization. created to make drinking water accessible to all. This charity is especially important to me because I live a privileged life where drinking water is almost always accessible to me. I could never imagine what others can live in their lives and I am dedicated to raising awareness of those who do not have a voice. My trip will highlight the importance of water conservation at the individual level – reduce showers, drink from safe sources, refuse to waste and enjoy the convenience of water in our society.

Stay with me on Facebook! https://facebook.com/skatecrosscountry

Follow the trip on the official blog! https://skatecrosscountry.com

You can help her achieve her goals here on her fundraising page.



Born in Vancouver, Les has been hiking and adventuring around the world most of his life. The practice of skateboarding facilitated travel, eventually leading to a long trekking adventure in Kenya. With a new appreciation for skateboards and some good relationships, Les has dropped everything to skateboard his life and, as they say, everything has changed since. Now editor at Skate [Slate] and one of the owners of Flatspot Longboards, Les is spending the rest of his time raising his first child, plugged into skate-web, and skating with Coast Longboarding.

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