Around the world on two wheels

Alumni Relations
Thursday 5 February 2026

Connor McElwaine (MLitt 2015) left his job in school leadership to embark on the adventure of a lifetime: a long-distance bikepacking journey inspired by a desire to understand the world and its history, which he first fell in love with at St Andrews. Connor is cycling across the world in aid of Venture Scotland.

I first arrived in St Andrews in 2008 as a prospective undergraduate attending an open day. My family members were excited by the prospect of me studying at the University and I had the exam results required for admission. Even so, I felt deeply overwhelmed and nervous about the idea of studying at such a historic institution and living in the town. Everything seemed so different to the people and places I was familiar with. I decided against St Andrews and in doing so, I was left with a feeling of wonder at what might have been. I couldn’t shake that feeling.

Curiosity unlocked

After completing my undergraduate degree in History at the University of Dundee, I decided to apply for a postgraduate course at St Andrews and, thankfully, was accepted to study for an MLitt in Modern History, graduating in 2015.

I will be forever grateful to the School of History for the education I received at St Andrews. It truly inspired my curiosity and unlocked a desire to continue to learn and to ask questions of our world.

I often think back to how incredible it was on a cold autumn or winter day to be walking down The Scores and into St Katharine’s Lodge to take out my notes and start a new page on what would always ben an enlightening discussion on everything from the Annales to Transnational.

I met many incredible people through my course and made some life-long friends. On graduating, I started at Teach First in 2015 and worked my way up to senior leadership positions in schools in London by 2018.

A big decision

In the summer of 2025, inspired in part by the world I’d come to know through my education in history and driven by a desire to live life fully, I decided to quit my job in teaching, pack my bags, put my belongings in storage, and embark upon an 18-month bikepacking adventure around the world.

As I write, I am in Jordan, heading to Saudi Arabia, and then onwards to Oman. My end goal is Australia and, who knows, perhaps a little further.

I’m doing all this for an incredible charity, Venture Scotland. Venture Scotland uses the power of the outdoors to transform the lives of young people in Glasgow and Edinburgh.

A man, Connor McElwaine, stands in cycling gear fixing a puncture to his bike at the side of a desert road.
Punctures and repairs by the side of the desert road

The adventure of a lifetime

It’s been an epic adventure so far and wherever I’ve been I have been warmly welcomed, offered food, a place to sleep (perhaps the stand-out sleepover was in an Iman’s garden!), enjoyed many laughs and countless cups of tea.

I’ve also cycled past many historical sites, learned from people about life in a whole host of places I would otherwise not have discovered, and heard their views on everything from history to politics, and the price of bread.

My journey has served has a powerful reminder that even when our world may seem alienating, fraught and dangerous, there are people in every corner willing to extend a gesture of friendship, kindness and warmth.

You can follow Connor’s bikepacking adventures on Instagram at @free_mcelwheeling.


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