Hitchhiking Stories From Scotland

In May 2014 I had the privilege of being a part of a hitchhiking race around Scotland.

Yes a race!

More on that in a second…

First I should let you know that my hitchin’ experience was very limited. A few short rides off a hiking trail in Costa Rica and Chile, a 10 mile jaunt to a nearby town once in Ireland, a few other random episodes but nothing over the top.

This race was an epic 546 mile quasi-circumnavigation. We had to visit 8 iconic Scottish checkpoints along the way and get photo evidence of our visit. Spots included various monuments, castles, and mountain views.

The idea of putting my total faith and trust into humanity in the hopes that we would somehow navigate 546 miles around Scotland was a bit intimidating. Ok, let’s face it…I was scared as hell!

I just couldn’t help being seduced by the adventure, and a chance to see a country for the first time in this unique way. Here was our route:


This race event was put together by Gary who heads up a beautiful group of NOMADS on Facebook.

Gary getting a thumb workout

Gary getting a thumb workout

To add another twist, I decided to do the race as a fundraiser for Pencils of Promise, an incredible organization that helps build schools for kids in developing countries. This had a two fold effect of helping kids while keeping me on track to actually finish (read not pussy out).

So there we were, on May 1st, 2014 standing on the side of the road, thumbs in the air and hoping for the best.

There was a lot of standing on the side of the road over the next few days, but not as much as I had imagined. We did all of the typical hitchhiker stuff. Smiled a lot, held out ratty cardboard signs, danced, sung terrible pop songs (ok maybe that’s not typical), put out as much good energy as we could to passing cars and hoped for the best.

photo (1)

In the end, My partner Gary and I proudly finished 2nd or 3rd (we aren’t positive) and hit all 8 checkpoints. Not too shabby:)

We didn’t really care too much where we finished, the race was an afterthought.

To describe the 3 days I spent thumbing around Scotland in one word, I would have to say that it was nothing short of transformative.

How can I possibly put this entire experience into words? I guess I have to so here goes….

When it comes to hitchhiking, you must depend solely on the kindness of strangers to get you where you need to go. You put yourself out on the side of road, stick your thumb out and hope for the best.


Each ride is an unspoken agreement of trust that needs to be decided on the spot. Driver’s size you up before they pull over. In turn, you open the car door and must judge if it’s a safe place to inhabit or if you’ll end up in various garbage bags at the end of the road.

When you jump in the car you share more than just a ride. You share personal space, stories and more often than not, authentic and beautiful connections with other human beings you would have never had a chance to get to know so intimately.

If you ever have any doubts about the generosity and overall goodness of human beings, just go hitchhiking.

Personally, I’ve never lost complete faith in humanity but have had times when my belief that generally people are good has been challenged.

Well, whatever parts of myself that were damaged by past situations in life have been fully restored through this adventure.

The ‘strangers’ who picked us up went out of their way to make sure we were taken care of. They treated us with respect and even admiration as we told our tale of the race and Pencils of Promise. Their kindness was overwhelming, and they seemed thrilled to give us a lift and be a part of this whole crazy adventure.

I wonder…

Does hitchhiking provide more opportunities for authentic connections, or was I just more open to connecting with people?

I still don’t know the answer, but I do know that being away from the digital world and the hustle and bustle of my ‘busy’ life gave me some undefinable spiritual boost and the chance for a more pure and fulfilling travel experience.

It took us 19 rides to go 546 miles, get to all 8 of our checkpoints and to the finish line.

The best way to give you a glimpse into our time on the road, and to share my gratitude is to take a moment to thank each ride individually.

Ride 1 – Barry. It was a short ride but getting the chance to blaze out of town, horn beeping while we passed and taunted other racers put a hug grin on our faces and made us feel like the race really had begun.

Ride 2 – Garreth. We chatted you up at the gas station, you looked a little skeptical but Gary won you over. After the ride you even gave us 20 bucks to Pencils of Promise. Thank you good sir!

Ride 3 – Nick. Thanks for teaching us about your cattle crusher. We had no idea it’s somebody’s job to flip cows over and give them manicures.


Ride 4 – I can’t recall your name but you are a busy guy. As manager of multiple distillaries you were just trying to get home to your family but took time for us anyway. WE THANK YOU!

Ride 5 – The old couple who literally drove 1 hour round trip out of your way just so we could get our picture next to the first checkpoint at the Cairngorm Mountains.


Ride 6 – Anka, we were thrilled when you picked us up but it only got better. You invited us into your home to meet your beautiful family and then fed us a world class meal. After that you drove us 14 miles to our next checkpoint on a night when you could have just been chilling at home. You’re a wonderful and kind person. Thanks to you, Jeff and Madison.


Ride 7 – A stroke of luck! We were planning on camping at Urquhart Castle until Johnathon and his son Joe decided to load us into their RV and take us all the way to the Isle of Sky hitting 2 checkpoints along the way. Brilliant!

Ride 8– Duncan Grant. We got to hear your DJ mix, story of travels to heal from your Mother’s death and the fact that you spent every penny you have a week ago on a boat named “NOMAD”! It was a pleasure to share the car with you.

Ride 9 – Micheal. You drove us a few miles down the road to a better spot and for that we thank you!

Ride 10 – The Belgian Couple. You were on vacation but gave us a lift anyway. Too sweet.

Ride 11 – Peter. You played the best music we heard on the trip and even let us snap a quick checkpoint picture. You dropped us in a great spot and went further than you had to. Thanks!

Ride 12 – The Aussie Woman and her 2 kids. Our 2nd campervan ride. You son was looking at us the whole way, he was adorable. So were the decorations in your bad ass camper. I want one of those someday.

Ride 13 – The sweet old couple from the Lakes District. You loved wildflowers and quilting and seemed very content together just cruising in your camper. Thanks for your kindness and trust.

Ride 14 – Lorne. You were, let’s just say…’interesting’. Still we appreciate the lift.

Ride 15 – Sarah and Ian. Thank you Sarah for taking us to your cafe and feeding us an awesome meal! A 5 star ride and lunch:)


Ride 16 – Keegan. You came at the perfect time, thanks for the lift my friend! Your dog was a little scared but he seemed to be ok when we left.


Ride 17 – Nicole. It was your first day of work and we were stranded on a country road. You got us out of a jam, thank you.

Ride 18 – Julia. You went above and beyond the call of duty. Where do I begin? You stopped on a busy road where nobody else would. Then you drove your work commute on a Sunday night when you didn’t have to just to get us to where we were going. Why did you decide to drive 2 strangers 45 minutes to the next town? Because you fucking rock, that’s why!

Ride 19 and our final lift – Wendy and Katie your 4 year old daughter.  Wendy, you never picked up any hitchhikers before,lord knows why you did this day but thank you for doing it! You took us all the way to the finish line. We wish you the best of luck in purchasing your B&B with your boyfriend. I know it will be a big success.


Also, cheers to my new friends, the other hitchhikers from the NOMADS group were some of the best souls I’ve ever encountered in many years on the road.


One final thanks to the country of Scotland. Your never ending beauty resides in both your people and your land.


Yours in adventure,


You're almost there!

Drop your email below so we can send your FREE course!

Powered by ConvertKit

Want to Travel More?

You need a plan. Sign up to access this mini-course The 3 Best Ways To Save Money For Travel, get exclusive content and join our amazing community of travelers. It’s all FREE!

You're signed up! Check your email to access the mini-course!