Five Cycling Challenges That Steered Me Into Adventure

How homegrown cycling challenges shaped the course of my adventurous life

In this article, I share the five self-created cycling challenges that have made me the adventure cyclist I am today. From the early days of a tough yet fun coast to coast cycle to a half-lap of the planet by bicycle – it’s been a heck of a ride.

Five Epic Cycling Challenges That Shaped The Course Of My Life

Looking back now to write this post it’s easy to see how I became a passionate advocate for adventure cycling. Over the years, I’d been slowly nurtured in the ways of bicycle travel by a long list of friends and authors. In particular, Adrian, my best-mate. We’ve done a lot of cycling together and these journeys are some of my fondest memories.

Long-distance bike journeys have helped me grow and to understand myself more fully. They’ve helped me after a romantic relationship breakdown, they’ve shown me that life is what we make it and that anything is possible if we want it enough.

fully loaded cycling challenges

But most of all, these cycling challenges have helped me to understand who I am and steered me towards a more balanced way of life that’s in tune with my true north. There’s a long tradition of spiritual awakening in bicycle travel literature, though it’s often framed in terms of love of the outdoors and reverence for nature.

I truly believe that exploring the world by bicycle has the potentiality to shape the people we become for the better. The skills we learn, the experiences we endure and the people we meet all reveal something valuable about our character. Let’s jump in.

Coast To Coast Cycling Challenge

My early experience of cycling challenges began with a group ride of the UK Coast to Coast. It was autumn 2008 and I was new to cycle touring. I’d ridden bicycles all my life but this was the first time that I’d taken off on a multiday bike trip in convey.

The friends I was in company with were a motley crew of experienced tourers and complete novices, like me. I rode a ridiculously small SCOTT USA sports bike that I’d loaned from my Dad. It was a 54cm frame with drop bars and a skinny saddle.

coast to coast cycling challenge

No gear, no idea

I had no panniers (I didn’t know what they were until the day of the ride), So I carried a rucksack stuffed with clothes and snacks. The bike had SPD pedals so I was clipped in for the first time. At the first junction off the train in Barrow-in-Furness, I nearly toppled off the bike.

This popular five-day cycling challenge followed a classic route that Adrian had planned for its variety, steep climbs and country pubs.  We crossed the Lakes, Dales and Moors, taking in the best of the northern English scenery. It was stunning.

By the end of the fifth day, I was a cycle touring convert. I knew then that bicycle travel as a means to explore the world was for me. I just didn’t know yet where it was going to take me.

the dunwich dynamo cycling challenge at the pub on the park

The Dunwich Dynamo

The Dunwich Dynamo is a classic cycling challenge in the UK. Famed for its turn-up and ride ethos, this 196km night ride has been running for more than 20 years thanks to Patrick Field of London Cycling School.

Known for the camaraderie between riders, this is one of my favourite organised rides. I’ve ridden the Dunwich three times over the years. The first time was just ahead of our European charity cycling challenge in 2011 and again in 2013 and 2014 while I was living and working in London.

The Dun Run as it’s colloquially known takes place on the summer solstice each year. Beginning in London Fields Park at dusk, riders from all over the country gather for a pre-ride pint at the Pub on the Park to shoot the breeze and to make final preparations for the night ahead.

cyclists on the beach at the lost city of dunwich

A beautiful madness

Up to a thousand cyclists each year ‘do the dun run’ with riders of all abilities rubbing shoulders and sharing the road as the giant peloton snakes towards the Suffolk coast and the final destination, the lost city of Dunwich.

A full English and pint on the beach are the reward for the tired first-timers. Experienced club riders often ride the route in reverse back to London. This is of course, totally optional, buses are provided and there’s always the train.

I’ve had some wonderful experiences on the Dunwich Dynamo. As Patrick would say if you ever chance to meet him, he’s interested in journeys. And that’s exactly what the Dun Run is on every level. It’s a night of beautiful madness.

20 countries in 100 days cycling challenge

A Charity Cycling Challenge owes its name to this prototype cycling challenge. In the heady days of 2011, Adrian and I were at a loose end and decided we might as well go on a bit of a bike ride. Slowly, over the course of a few weeks, the idea evolved into a charity cycling challenge.

We shared with friends the possibility of going on a multimonth bicycle tour and before we knew it we’d quit our jobs and were on a ferry to Rotterdam. Our self-made sponsored charity bike ride became known as 20 Countries In 100 days.

wild camping in the black forest

20 Countries In 100 Days

As the name suggests, we set our sights to cycle through 20 European countries in 100 days as a means for setting the challenge parameters. The original plan was a coast to coast in the USA, though the flights, logistics and seasons were prohibitive for our dates.

We preferred to cut the flights to add environmental awareness element to the cause since the bicycle is a very green mode of transport. We sailed to Rotterdam at the and of July 2011 after a long goodbye at Glastonbury Festival and the Secret Garden Party.

Once we arrived on the continent we had a funny half-hour in Rotterdam where we basically had no idea what we were doing next. We’d got this far on pure excitement and adrenaline. Now that had worn off we found ourselves at the tourist information bureau in search of a map and a plan of action.

cycle tourers at the rheinfall

A Cycling Challenge Of Our Own Invention

The beauty of inventing your own charity cycling challenge is that you make the rules as you go. Map in hand we simply set a course due East and made the rest up as we went along. Adrian is a seasoned pro with a map. He figured we’d ride a big loop out towards Turkey then back again.

Starting with the EuroVelo 6 at its origin deep in the Black Forest then following the Danube river for a while, occasionally breaking off to visit local towns for provisions and some Alpine climbs. This pattern we repeated mostly to the terminus of Europes longest cycle path to the cusp of Serbia and Romania.

alpine switchback

A Wrong Turn

A wrong turn on a sleepy Sunday morning took us south to Bulgaria rather than further onwards into National Park Djerdap. So we drifted ever south to Greece, to our furthest point Eastwards for a lap of the Greek Island of Thassos. Then began our slow pedal along the Adriatic coast to Slovenia and our 100th day.

We ended the trip in Llubjana since we’d completed our sponsored bike ride with 22 countries in the 100-day time limit. Our fundraising efforts had shipped a container full of second-hand bicycles to Africa via the bicycle charity, Re~Cycle.

We celebrated with friends in the city with some hiking and beers. I had a fleeting moment where I considered the possibility of continuing onwards to Vietnam to meet up with an ex-girlfriend. But alas, I was stony broke and this would have to wait.

cycling challenge in morocco

Morocco By Bike

Morocco by bike is our fourth of five cycling challenges that steered me to adventure. Following the success of our European ‘Grand Tour’ Adrian and I were keen to explore a new continent. A short ten-day trip to Morocco was planned as our next cycle tour.

This cheeky cycling challenge was a fast-paced romp from Marrakech over the Atlas Mountains via the Tizi n Test down to Agadir then up the coast to Essaouira before scootching back to Marrakech.

One of the great learnings of cycling in Morocco was that the climate was drier, the roads less well paved and the hospitality even more generous than in Europe. Armed with these facts we were ready for a cycling trip anywhere in the world.

cycle touring in india

A Half Lap Of The Planet Cycling Challenge

Immediately following the 20 countries in 100 days cycling adventure, Adrian and I both moved to London. It was a natural progression from our time as students and young graduates in Nottingham. The Big Smoke was calling.

During the three years and there months that I resided in the capital, Adrian and I made many more ten-day trips and long weekends. Not to mention the regular mountain bike trips around the UK.

We were by now, fully-fledged cyclists. We even made our own fixed gear bikes like the Hipsters we pretended to be. Poncing around East London supping premium craft ale through freshly trimmed beards.

cycling in burma

Leaving Las Engles

For the three years I lived in London I spent a great deal of the time trying to convince my girlfriend, Rosie, to join me on a round-the-world bike ride. Alas, having already travelled quite recently (she’d just returned from a round-the-world backpacking trip when we met) she simply wasn’t into it. Rosie wanted a house and a baby. I offered a tent and a bike.

Adrian had met a lovely lady and was happily settled into London life. My next cycling challenge would be a solo expedition. Despite the best efforts of friends, family and work colleagues, I quit my job and left town to go on a bike ride.

This is the potted history of how self-made cycling challenges steered me into adventure. As with any life-changing decision, there’s an element of risk. I’d sacrificed conventional success and stability to see the world on my own terms.

As the Latin proverb goes, ‘fortune favours the brave’. And in my experience, it’s true. Rosie once wrote on the wall of my office a quote from Goethe;

‘Whatever you can do or dream you can, begin it; Boldness has genius, power, and magic in it.’

I couldn’t have asked for a better parting gift than that.