Trans-America Cross Country Skate

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Raised by 27 people in 12 months
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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
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Hey everybody!

Thank you for being a part of Skate Cross Country! Almost 10 months and several adventures later, I finally created, wrote, and designed my first book detailing the journey in all of its morbid, hilarious, and struggling detail.

As a way to say thank you for helping me achieve my dream, I am including your name (no matter your contribution size!) in the "Special Thanks" page along with the people who helped me get along from the west coast to the east coast by skateboard. Your support meant a lot to me and this is just one way I can offer a way to show my appreciation.

The book is a photobook and I am doing presales through Kickstarter - if you'd like to get a copy and see your name as a huge piece of the story, check it out at the link below!


Once again, thank you, thank you, and thank you for your support!
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Hey everybody! What a crazy return to society it has been.

First and foremost, the achievement of making it from Oregon to Massachusetts with nothing but a skateboard, backpack, and support from friends and fans has been an absolutely eye opening experience. As you can imagine, I've had a wild time adjusting back into my home state.

Almost instantly I pushed myself back into the work force with a retail job to put some cash in my pocket. Being in Massachusetts, I was pummeled with snow and below freezing temperatures, making training and skating difficult. That has been quite difficult to adjust to.

As I pieced myself together to make way for my next goals (Ultraskate 2018 and more adventuring), I made room to take on my next challenge: I will be skateboarding from Miami, FL to Jacksonville, FL just days after recovering from the Ultraskate. The idea in life is to never stop achieving my dreams, and as I do, to continue making new ones. I hope that my tenacity for finding my place in the world will inspire others to do the same!

I closed this GoFundMe fundraiser to open up a new one. As we learned skating across the country, I couldn't have done it without you, or the people I met along the way. I hope you will find it in your heart to share with me so I can continue to push for others to reach their highest potential.

Many articles have been written about me on various news networks since my triumphant return to Massachusetts. Most have highlighted the fact that as a transgender individual, the ability to push forward through uncharted territory never wavered. I hope to continue that trend with my Florida skate, and potential new Personal Record (PR) at the 2018 Ultraskate. Remaining and defending my title as a top 3 women's competitor in distance skateboarding is a stride in athletics for all women, transgender or not. Gender has never decided how well we can perform and I aim to continue to prove that.

Please follow this link: https://www.gofundme.com/transflorida-skate-fl and check out the details of my upcoming journey. I hope to see you out on the road!
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I want to make a very public thank you to everybody and every brand that helped me with this adventure. Never in my life have I ever felt so overwhelmed with love- Many of you watched along through Facebook and my blogs, rooting me on and offering me assistance all along the way.

I reached the Boston Marathon finish line on Day 48- A day made possible with four wheels, a wooden board, a backpack, a positive attitude, and many, many new friends along 15 states. Skating over that finish line marked the first time I ever achieved anything I set my mind to.

I did not become the first to do anything, nor did I set any world records. Many factors came into play with that, which I would like to address. First and foremost was the extra ambitious time I wanted to finish in. It was very far out of reach to try and make that happen. From being on bed rest with a high ankle sprain until the day I actually departed, the weather, the pavement, and the shortening of daylight, there was no hope. Additionally, I now know that in order to accomplish a world speed record for something of this caliber, it would be helpful to have friends come with you, whether that is in a follow car or just a buddy to skate and draft with.

Right on day 1 I threw out the hope of setting world records. It was preposterous to think I could skate with my head down and ignore the amazing people I ran into along the way. Every single state bestowed their greatest individuals who showed me limitless kindness and I will always be forever grateful. The experiences I had and the friendships I forged will be everlasting, and will always mean so much more to me than a world record ever could. And even beyond that, I made friends through social media whom I never met that became very close to me. Some days, it was just nice to know somebody was checking in on me.

Now I am back "home" where I grew up. Many people say that home is where the heart is, but I'm pretty sure I dragged my heart along the entire country and left the pieces behind. I will always have a free roaming spirit and am very much looking forward to planning my next adventure. I have no idea what it is or how I'll make it happen, but I know that between you, my funders, my fans, my friends, and my loved ones, I will figure it out.

Beyond any reasonable outcome from all of this, I learned one thing: The world is a good place. I strongly encourage everybody to leave their comfort zones at least once in their life. As a transgender woman who took on a great challenge, I can say with confidence that there is hope for all of us. I would like to help anybody I can with finding a way to pursue their own dreams.

Though I am now twice as lost as I was when I began, I gained too much to feel any other way besides proud.

From the bottom of my heart: THANK YOU!
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Today is my last day in Idaho. I am relaxing at a ranch with some nice farmers who, despite closing the campground, have opened up their yard to me next to the power outlets. I have been eating good. Depression eats at me as the world doubts my being and cause, but I know how many voices have crossed mine and wished me the best. The world is a good, welcoming, and amazing place. I will never change my mind, even though I doubt myself.

When I ditched my cooking gear it vastly changed how I am able to complete this trip. A lot of my days have been spent traveling between towns and hoping a cafe is open. As I proceed into Wyoming, I will have less luck with finding places to eat. There is no doubt I will go hungry. But, the human body can withstand 3 weeks without food, and I am only counting on 10 days to make it to Nebraska.

Idaho was a challenge and tested my will and motivation to a point beyond repair. Though I met many amazing people, the broad lands and other factors truly beat me down. My confidence has been shaken. I wonder with each push if what I am doing is worth anything each day. I see the accomplishments of others and feel I don't compare. Waking up and pushing into the headwinds has brought tears I didn't think I had. It only gets more challenging from here.

Bare bones, I'm just as committed to basking in the San Diego sun when I finish as I ever was- quitting was never an option and I had never truly considered it. My head has been spinning and out here in the west I am without a shoulder to stand on.

That all being said, Wyoming is not only a challenge, but a threat. I can imagine that 7000ft of elevation will force me into motel rooms because of wind or snow- as much as I'd love to truly survive on my own, in the interest of a lighter pack I am without the proper tools. I have no doubt that these challenges will pass as I head more east and get out of the high mountains.

I am asking my family, friends, new friends, acquaintances, and friends to be for anything they can spare as I delve into what will be my truest test. I take to heart all of the support I have been given in prayer, spirit and help, but at this crossroads I am without option but to beg for assistance while I cross my first third of the distance. Beyond the snowy west, camping and foraging is something that will be infinitely more accessible.

Please let me know what I can do out here on the road for you in exchange for your monetary offerings. I have an endless amount of love to give, to match the love I have been given.
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$1,160 of $2,000 goal

Raised by 27 people in 12 months
No Longer Accepting Donations
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