Trans-America Cross Country Skate With Calleigh Little

Calleigh Little has been making a name for herself in downhill, including taking first in the Central Mass Downhill Ladies class. What tends to be the most talked about aspect, for better and worse, is the fact that Calleigh is a Trans-athlete. Frankly we don’t care how she wants to identify, just the fact that as a skater, she is smashing barriers and doing so in style and grace. And in her fashion, she is now taking her self across America by skateboard and looking for your awareness and support as she chases her goals. Support her journey here.

From Calleigh:

Hi there. On October 9, 2017, I will embark on a cross country skateboard journey from Bend, OR to Boston, MA. This video is a short introduction into what it means to me to complete the ride, the inspiration, and a short about me. With thanks to Original Skateboards, Orangatang Wheels, and newton Trucks for their continued support in my endeavors. Nothing but the best beneath my feet from the West to East. Support her journey here.

Check out her setup:

Here’s a bit more from from Calleigh’s Fundraiser page:

My name is Calleigh Little. I am a 26 year old transgender woman from Boston, Massachusetts. I have been skateboarding for upwards of 6 years, and competing 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 Women’s)
188 miles – Chief Ladiga Sk8 Challenge (First Place Women’s)
138 miles – Boston, MA to Provincetown, MA
100 miles – Milford, MA to Satan’s Kingdom, VT
Bend Beatdown – 5k 3rd Place Women’s/10k 2nd Place Women’s
Adrenalina 2016 – 2nd Place Women’s
215 miles – Miami Ultraskate 2017 (Second Place Women’s)
188 miles – Chef Ladiga Sk8 Challenge (Second Place Women’s)
Central Mass Skate Festival 8 – Women’s First Place

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


Competing in women’s sports has been an amazing experience for me. I have learned a great deal about what it means to be transgender over the years of pushing myself beyond the limits. I have experienced being the only transgender racer in distance skateboarding, and I hope to pave the way for others like myself to feel confident to be their true selves in an accepting world. I can only hope that my determination to pursue my dreams will inspire others to do the same.

Upon completion of this trip, I will succeed in landing the following world records:

-First Transgender Person to Cross the USA by Gravity Powered Travel
-First Woman to Skateboard Across the Country Solo
-Fastest Known Time Skateboarding Across the USA

This journey is entirely unsupported – there is no car following me, no shelter provided, and only my will pushing me to complete it.

Your donation to this cause will go a long way. In addition to granting me access to necessary survival tools like food, water, and shelter, a percentage of your donation will be given to Water.org – a charity created to make safe water accessible by everyone. This charity is especially important to me because I live a privileged life where potable water is nearly always accessible to me. I could never fathom what others may go through in their lives and am dedicated to raising awareness of those without a voice. My trip will highlight the importance of water conservation at the individual level – reducing showers, drinking from safe sources, refusing to waste, and appreciating the convenience of water in our society.

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

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

You can chip in to help her accomplish her goals here on her fundraiser page.