A Path of Fearless Exploration and Wild Creativity: Ali Bortone’s Story

Ali Bortone is a thru-hiker, the owner of AK Art Factory, and the designer of the original Legacy Backpacking logo. If you visit Alaska there’s a good chance you’ll see someone wearing one of her hand painted hats. She’s painted over 16,000 since 2011 and has become famous in the Anchorage area. Each one is unique with its own design; it may be a mountain scene with a Gnome beside his Mushroom House, or Sasquatch beneath the Northern Lights, and no two are the same. You can find her work at akartfactory.com. Legacy Backpacking is proud to have Ali as its chief designer and to share her story.

What is your hiking experience?

I fell in love with hiking in high school. I’d take my family dog and we’d head out to trail solo. It probably wasn’t the smartest idea, considering there were mountain lions and bears out there, yet it became such a meditative experience for me. I loved the feeling of being in the mountains, jumping in rivers, and challenging myself just for me.

When I moved to Alaska in 2010, I bought my first real backpacking backpack, a green Gregory. I knew I wanted to live out of it, even if just for a while. During that time of my early 20s I’d wake up and run up mountains before work, often still going solo. I started organizing overnight trips with friends, rallying my girlfriends to throw on heavy packs and follow me into the wilderness. It became my rhythm—and that early connection to hiking has shaped my life in so many ways since.

Ali’s first thru-hike was the Te Araroa, a 2,000 mile trail in New Zealand leading from the Northern most point of the North Island in Cape Regina to the Southernmost point of the South Island at Sterling Point in Bluff. Prior to her thru-hike of the TA she backpacked in Colorado, on the island of Kauai, and took multiple multi-day trips in Alaska.

What was the Te Araroa like?

WHEWWWWW…

The TA was a life altering experience for me. It’s been the hardest and most rewarding endeavor I have ever done.

It started on 90-mile beach with physical pain, sore legs, numb shoulders, swollen feet, hunger and sometimes total exhaustion. Throughout the trail I became physically stronger and found that it came time to train my mental strength. It’s funny how walking for months can help you process life, past trauma, and what you really want out of life. After that, this sense of peace and freedom took over- moving toward a spiritual side. The TA was everything- wet feet for days, slippery knee-deep mud, hard road surfaces, killing swarms of sand flies in the tent, careful steps, and hunger. It was four pairs of shoes and toe socks. It was waking up next to the love of my life in our cozy tent and sipping coffee in our sleeping bags while mustering the courage to put on our wet shoes and socks and working together to walk across a country, taking turns exchanging energy and sharing a once in a lifetime experience, making our relationship even stronger. It was jars of peanut butter, OSM bars, star gazing, summiting mountains, walking through rivers and losing site of the trail markers. It was exhaustion and the highest highs I’ve ever felt. It was eating whatever I wanted while being in town. It was fully appreciating a shower and a bed, a clean change of clothes and some delicious Indian food. It was meeting strangers on trail who turned into great friends, accepting and supporting each other at our lowest. It was meeting locals who would give you the shirt of their back, a car ride, and even cracking open a sea urchin and a beer to taste. The TA was absolutely wild and the greatest adventure of my life. Stripped of everything except the pack on my back the trail was a sense of total fulfillment.

Why did you pick the Te Araroa rather say another trail?

I’d always wanted to go to New Zealand, and the timing worked out perfectly, their summer is our winter, so it was ideal for a long-distance hike during the colder months back home in Alaska.

Another major draw I had was that there are no predators in New Zealand. No bears, no mountain lions and while Australia has most of the deadliest snakes in the world, New Zealand is one of the few countries that’s completely snake-free. The worst thing the islands have to offer are the absolute hellacious demon sand flies.

What is your favorite trail?

New Zealand takes the top. Especially:

  • Waiau Pass

  • The Queen Charlotte Track

  • The Richmond Range

But in Alaska I’d say:

  • Rabbit Lake

  • Mt. Marathon

  • Trails in and around Denali

What's been the best day on trail?

On the north side of Waiau Pass we waited out a storm in a hut with other hikers, watching waterfalls form down the cliffs. The next morning we woke up to snow and hiked through frozen streams and across snow covered rocks. We saw five Keas (birds) and descended into a lush forest below snow line. With bluebird skies the next day, we climbed 2,000 meters straight up the mountain with stunning views and ended with the long day a dip in the river. I was smiling so hard as we layed in our sleeping bags.

What’s been the worst day on trail?

It was day four on 90-mile beach with just one more day left of walking on the concrete like sand before we’d arrive to the town of Akirai. The scenery never seemed to change; beach on the right, sand dunes to the left, and the occasional truck or tour bus passing by. Tyler and I had just a few more kilometers to the campsite but my feet were in so much pain I could hardly walk. I was on the brink of tears. I tried to trick my mind by counting, 1..2..3..4..5… with each footstep eventually to 100. I’d then would look up only to find nothing had changed. Determined, I looked down and counted up to 100 again, and again, and again. Finally, we turned toward the camp site which led us down a road. I was hobbling like an old turtle walking so slow. It was frustrating because all I wanted to do was stop hiking. Finally we made it. I was silent and my boyfriend could see the pain in my eyes, he set up the tent for us and then went to go get some more information about showers. As soon as he left I went to take my shoes off and found it difficult to pull my feet out. I took my socks off and saw that my feet were swollen, sand fly bitten, and blistered. I broke into silent tears of pain. This wasn’t normal for my feet. I couldn’t even fit my feet into my crocs. I thought, could I hike 2,000 miles? Could I really walk across an entire country? What if my body is giving up on me and this grand adventure is over before it really begins? The other hikers in the campsite seemed to be just fine, laughing and gathering together to cook and talk about the day. I didn’t want to disappoint myself nor disappoint my adventure partner. I went to sleep thinking my feet would magically heal overnight.

Tyler and I awoke the next morning, and Tyler asked to see my feet. He took one look at them and said, “Yep, we need to go to the hospital.” I felt so defeated, immediately I wanted to ignore it and just tough it out.  Luckily we met a cheeky kiwi who offered to drive us into town where they dropped us off at the hospital. 

With three days of rest, my feet up with an ice pack covering them, and some antiseptics, I was able to continue. We picked up trail where we’d gotten the ride from and finished 90-mile beach. Redemption! I would like to say that after that my feet were fine, but to tell you the truth, it was weeks of thinking of nothing but how badly my feet hurt. I found that the solution was to buy bigger shoes and the pain began to lessen.

The moral of the story kids is, buy bigger shoes, and remember that things are temporary and can always get better!

What's it like hiking in Alaska? What locations are a must visit there?

Hiking in Alaska is breathtaking. The wilderness is endless and raw. In summer, with the midnight sun, you can hike well into the night and still have daylight. On certain days the time between sunset and sunrise is an hour.

Of course, sometimes you can get a little “bear-anoid”... especially when you see one nearby. There’s an eerie, humbling feeling that comes with knowing you’re not top of the food chain out there.

The trails can involve bushwhacking, swarms of mosquitos, and steep climbs—but they can also deliver the best day of your life. Alaska is filled with alpine lakes and rivers everywhere to wash off, cool down, or just sit beside and soak it all in. Alaska is a land to be explored.

Favorite hikes in Alaska:

  • Rabbit Lake

  • Little O’Malley

  • Denali Park

  • Kesugi Ridge

  • Lost Lake

  • Crow Pass

  • The North Face

  • Mt. Healy

  • Mt. Marathon

Places to visit:

  • Girdwood

  • Seward

  • Talkeetna

  • Homer

  • Denali National Park

  • Byers Lake

  • Eklutna Lake

  • Kenai Lake

  • Cooper Landing

And if you get the chance to get on a boat and head into Prince William Sound—do it! It’s like a whole other Alaska out there, and the nature out there will NOT disappoint.

Any advice for future long-distance hikers?

My advice is that you don’t need to be a pro-hiker to hike a 3,000km trail. Most long-distance hikers use the first month of trail to get in shape and gain their “trail legs”. Also listen to your body and take breaks when it tells you to. Bring a good attitude as often as you can, go light, and bring more snacks than you think!

Most important, in the post trail aspect, is to write down your experiences and feelings, you can only remember so much of what was occurring at the time while looking back on just a photo. Also take more photos with yourself and other hikers in them! So many you’ll find it was just another photo of a tree or scenic view and you’ll find yourself wishing it was a photo of friends.

Get wide toe shoes +1 size bigger. Toe socks and moleskin go a long way!

Soap and one extra pair of “clean” socks will make a world of a difference.

How did AK Art Factory begin?

I have always loved to paint, but my true love for it began when I was in high school as a way to grieve after my mom suddenly passed away. Fast forward to 2011, I was living in Girdwood, Alaska. I wanted to sell artwork at the festival, Forest Fair, but I wanted something more to paint than the average hang on the wall canvas. It didn’t feel like my style. I was working as a lift operator at the local ski resort and while sitting at the top shack of a chairlift the idea of trucker hats came to mind. I ended up painting fifty hats for that festival which all sold (mostly to my friends). Soon after that, businesses in the area began to order from me and more people wanted hats. I was inspired by a friend to get a business license and decided to make a Facebook page. I felt no way near ready for what was to come, but I went for it. Seven years later it became my full-time occupation and I was able to quit waiting tables and fully focus on my art. While hiking the Williwaw trail in Anchorage, I came up with the name “AK Art Factory” and thought it had a nice ring to it!

What is your process of painting hats?

Step 1: Order hats from wholesaler

Step 2: I take a sleeve, or two, of twelve hats and paint the background- usually a sky and mountain scene.

Step 3: I take all of the hats with the finished background and paint the details onto the mountains, adding; animals, trees, a moon or sun, a little trail, or a river. During this step I don’t have a full plan of what I will paint, I just add what feels right.

Step 4: The hats are then released out into the world! I truly feel that each hat is made for a specific person.

Step 5: Repeat! Repeat! Repeat!

Since 2011, I’ve painted over 16,000 hats, averaging 1,200 a year. I see one or two every time I am out and about in Alaska. It’s surreal! Thank you to everyone who’s shown me so much support!

Is there any piece of artwork that you’re particularly fond of?

My favorite piece I have done is a mural on a box truck. It was for a sailboat charter company, and the truck was 7’x11’.

Do you only paint hats?

I love painting on other surfaces too! The hats have just taken over! Every now and then I get an opportunity to paint on moose antlers, airplane propellers, t-shirts, walls, box trucks, guitars, shoes, and more. Any surface can be an open canvas for art.

Is there anything you'd like to do with your art that you haven't yet? Say, goals for the future?

I hope someday to transition into creating artwork for outdoor gear such as backpacks, sleeping bags, tents, and clothing. I like to think that each hat is practice for the “big dream” and when the time is right and the stars align, it will all come true!

Any advice for beginning artists?

Each one of us has the ability to be an artist, all it takes is starting! Dedicate time every day to build your skills. Sometimes painting is the last thing in the world I want to do, literally I’d rather do anything else at those times… but one day, you’ll look back and see how far you have come. Skills take time and dedication to improve. It won’t happen over night or because you want it to. Also, don’t be afraid to promote yourself or your artwork out into the world. You’d be surprised at the positive reactions you get when people see your unique style. It can be scary, and you can never be certain about what will happen, but art is a beautiful and meant to be shared. Art is a way to heal, to process, and to meditate… kind of like backpacking! Do it for you and don’t think too much, just let your body and intuition take hold and see what is created. Lastly, Artificial Intelligence is taking over our world it seems, don’t let that deter you. Original art will always be cherished and has been since the first cave men took tiny rocks and started sketching onto the walls of their caves! 

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From Trail to Tide: One Man’s Journey Around the World