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How to Skateboard from Dusk ’til Dawn

Today we have an article written by Lauren Rains from Outdoor Minded Mag (for whom I wrote an article last year). Lauren has, rather flatteringly, gone to the effort of formatting her advice article about skateboarding in the style of a Next Challenge ‘How To’ guide. Over to Lauren…

How to Skateboard from Dusk ’til Dawn

THIS ARTICLE: Offers a basic overview of how you might go about skateboarding between two locations for a one-day microadventure. It highlights the likely difficulties, explains gear/equipment/level of expertise needed, and a few lessons learned from my own personal experiences. It also covers how absolutely awesome it will be if you embark on a skate trek like this!

My Experience

I am not an expert skateboarder by any means. In fact, I only started skateboarding about two weeks before I embarked on my first 30 mile skate trek. This isn’t climbing Mount Everest. You don’t need thousands of dollars in proper gear, or months and months of training, or years of planning, or professional guides and resources. You don’t need any of that! All you need is a little bit of balance, some strong legs, a board with four wheels attached to out, a sense of adventure, and a little bit of cajones to not fear the pavement once you pick up speed!

In 2012 I skateboarded between Boulder to Denver, Colorado. It was a 30+ mile, 12 hour journey that started at 8:30 AM from my apartment’s front door and ended at 8:30 PM in the center of downtown Denver. I printed out a backroad bike route between the 2 cities I found on a Google image search, and on I went to see what surprises I would find along the way.

What I offer here is the perspective of someone who goes on adventures for the sake of adventure and personal conquest – I’m an enthusiast struck with wanderlust, not a professional athlete or a paid professional. This is how you can embark on a similar microadventure from wherever you’re based, and what I’ve learned from my experiences so far. Here is my advice…

1) Starting With The Mental Game: Anyone Can Do This

Whenever I tell someone about my 12 Hour skate trek, I usually get one of the following responses:

  1. “WTF are you crazy?!”
  2. “Actually that is awesome!”
  3. “But I could never do that..”

But in all honestly, it’s not that difficult! It’s much more about your mental strength than your physical strength. You don’t need to be an expert skateboarder by any means! If you take a few weeks ahead of time to practice and get comfortable on the board around town, 1 mile is no different than 30 miles… for the most part. ;-)

2) Choosing your Start & End Destination

You don’t necessarily have to start from your apartment door like me. I once did a skate trek in Saint Augustine, Beach FL I called “From Sea to Marsh” as I began at the coastline of the Atlantic Ocean and went west until I hit the Saint John’s River which was about 30 miles away.

You could make your start – end points:

  • 2 cities like I did from Boulder to Denver
  • 2 famous landmarks
  • Directly across a city
  • Around the circumference of a city
  • Through a well-known part of a region or national park
  • Towards some sort of goal (e.g. skate 30 miles in search of a city X’s famous  food/landmark/vista/sunset etc.

3) Terrain: Flat, Hilly, Urban, Country, Highway, Backroads

The terrain of your trip is what’s going to be the biggest factor in determining the difficulty of your skate trek.

For instance, when I did the Sea to Marsh skate trek in FL it was 30 miles of the flattest terrain in America. This required a lot more pushing, a lot more effort, and a lot more, well, pain in my legs.

On the other hand, the trek between Boulder and Denver was much more hilly, which presents its own set of challenges: skateboarding down a sidewalk with cars rushing past you is pretty scary to say the least. There were times when I finally sucked it up and sat down on my board bobsled style using my foot as a break. It must have been quite entertaining for passing cars to see!

Before you embark on your journey do as much research on the terrain as possible. This isn’t my strong suite and I’ve managed to get from A to B both times without much research, but I’m fully aware I could have avoided some roadblocks and been better prepared had I looked into this stuff ahead of time.

4) Gear: Get Comfortable Shoes

I had to stop at the store in the middle of my trek and get a new pair of shoes because the ones I chose to use were absolutely rechid. And it was because of pure laziness. I had lost my shoes while moving a few weeks before and instead of getting new ones I chose to use an old pair I had laying around.


Get a decent pair of skate shoes or padded sneakers. This is a high impact sport on your feet and legs, and it’s very easy to injure yourself skateboarding.

5) Gear: Decisions when buying your Skateboard

I used a longboard from OZ Boards for this trek as my sponsor. Whatever board you get, you’re going to want to make sure of the following:

  • Brand: Get a board from a company you support. I felt really good about using this board along the way because of what it stood for.
  • Bearings: Make sure that the bearings are new and clean – this is what makes the wheels able to turn effortlessly as you push. If they’re old, dirty or rusty the wheel won’t turn as much, and you’ll be pushing a heck of a lot more.
  • Board: You’re going to want to do this in a longboard: 36 inches give or take is a good place to start. As far as board shape goes, drop decks are great for long distances, but your classic longboard shape is fine too, which is what I used.
  • Rise: This is how far off the ground the board is. Because our goal here is distance and not tricks, having it closer to the ground will allow you more control and less wobble.

6) Teach yourself to push with BOTH legs

This is absolutely essential. Could you imagine skateboarding for 12 hours straight pushing on the same leg over and over and over again? Your leg would fall off after first turning to completely jelly.

Take the time to learn how to push with both legs before the trip. It’ll seem really awkward at first to be pushing with your less dominant leg, but after a few hours of practice, you’ll be good to go.

Do not skimp on this lesson. It will make or break your trip!

(I have a sneaking suspicion that legendary skater Dave Cornthwaite may have skated the length of the UK only being able to skate with one leg, although I’m not sure he’d recommend it! – Tim)

7) Enjoy the process of a microadventure

This is not going to be all roses and butterflies. It’s going to be a huge challenge and you are going to hit roadblocks. It’s likely that halfway through you’re going to want to call it a day, just as it’s likely that you’re going to feel the urge to rush to your final destination due to the fear you might not make it there in time.

All of those feelings are an essential part of the adventure. They are what make it challenging, both mentally and physically, and therefore, so rewarding.

So throughout the day, don’t forget to stop and smell the roses. Take in the sights around you and listen to your senses. Think about everything you’re seeing, feeling, smelling, stating, touching.

Your skate trek will be over before you know it, and you’ll be wanting to start all over again by the time you hit point B. Trust me. So enjoy every second of it, take it all in, and be in the moment.

Finally, I would like to mention Oz Boards and Solepack since they helped make it happen! Super great people behind both of those small companies – very dedicated entrepreneurs.


Have any other questions about doing a skate trek microadventure? Shoot me an email anytime at [email protected] and I’d love to help you get it going!


To read more about Lauren and all things outdoors, visit

You can also read about her other microadventures like her 50 Mile Walk Along the Atlantic and other projects on her blog at

For more advice on skateboarding, check out Dave Cornthwaite’s 10 Tips for Your First Skateboarding Expedition.

About the Author

Tim Moss has supported over 100 expeditions across all seven continents. He has climbed new mountains, crossed a desert and recently cycled 13,000 miles around the world. He is a Fellow of the Royal Geographical Society London and a Guinness World Record Holder. He aims to encourage more people to live adventurously. Read more...

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