Race or Ride? Taking a Detour in South Wales with Tailfin

Phil Dobson
2 days ago
4 min read

When James Bracey and I met, we bonded over the opportunity to diversify cycling. We sat chit-chatting at a partner meet for Team Amani, and that shared spark was a reminder that moving this needle can start with a single conversation.

Fast-forward a few months, and we conceived an idea for a partnership. Enable underrepresented groups to experience bikepacking as it was made to be done, the Tailfin way. Detours was already firmly set in the calendar, Cycling Culture Club jumped onboard. Enter Phil Dobson, founder of UpCycle London. A visionary in his own right and a curious and adventurous bike rider. He agreed to explore what bikepacking could offer and tackle Tailfin's first Detours event. His experience, I expect, is one many of you will be able to share.

To learn more about Detours, jump over to Tailfin.com

Enjoy!

Miles, CCC Founder

I'd only been to Wales once before, on a Year 8 geography trip. Back then, it was all diagrams of rivers and half-asleep coach journeys.

Thanks to the Cycling Culture Club, I was given the opportunity to come back and take part in the inaugural Tailfin Detours event in the Bannau Brycheiniog National Park. They lent me some kit so I could experience this new kind of ride, part adventure, part challenge, where you choose your own route and chase checkpoints against the clock.

From the start, the event made you think.

Detours rewards the adventurous and the brave; you pick your own line, rack up points for each checkpoint, and hope you don’t get caught out by the clock.

As usual, I left things until the last minute, so the night before I got the train down to Newport, I was glued to Ride with GPS, plotting and re-plotting my route. Working out where to resupply, which climbs to attempt, and what to do if the weather goes sideways. I gave myself options: Race Route A, Scenic Route B, Sensible Bailout C, knowing full well the day, my legs, and the weather would make the final decision for me.

Into the Mist

Early Saturday morning. I’d stayed the night in a little town halfway between Newport and the campsite, so I rolled out along the Ironworks cycle path feeling half-fresh, half-nervous about what was ahead. Five minutes in and the heavens opened. Typical. I pulled over, opened up my AeroPack and threw on my waterproof jacket.

By the time I’d got it zipped up, the rain stopped. Wales having a laugh at my expense. Back on the bike, I wasn’t entirely sure I was heading in the right direction until I spotted the flash of a red light up ahead, another rider already making their way up the climb. At least I was on the right road, even if it was straight uphill into the mist.

I arrived at the Tailfin campsite just 10 minutes before the rider briefing. Just enough time to register, catch up with a couple of familiar faces and stock up on Styrkr bars, then we were off. The mood was light, but I could already feel the race-versus-ride tension bubbling away.

Was I here to smash checkpoints as fast as possible, or just to enjoy whatever came my way?

Most riders headed straight for the nearest checkpoint. A mystery, nobody could find it. After a couple of discussions, some riders decided to push further up the hill, while others stopped to take selfies as proof they made it to the coordinates.

Checkpoints and Setbacks

I pushed on to the second checkpoint, a church perched at the top of a short, steep hill. Just as I arrived, pssssst, puncture. Sitting in a churchyard fixing a flat in the rain felt strangely fitting.

Bikes have a way of humbling you, reminding you who’s really in charge.

Inner tube replaced, I powered on to the mandatory checkpoint at the top of Gospel Pass. On the roads leading up to the climb, I saw a few riders going in the opposite direction. What did they know that I didn’t? Just as I reached the foot of the climb, the sky opened again, rain hammering down. I thought about my upcoming trip to Rwanda, the climbs, the heat, the sheer scale of what’s coming, and realised how valuable this weekend was as the perfect test.

The challenge wasn’t just physical; it was mental. Do you chase every checkpoint? Or do you give yourself permission to bop around, bump into the same riders over and over, swap stories, and see where the road takes you? That’s the joy of this event. The race is there if you want it, but the ride is what most of us actually come for.

Decision Time

Mid-afternoon, I stopped for coffee in Hay-on-Wye. This was the key decision point: head west for a couple more checkpoints, or play it safe and head straight back to camp. With the 6 pm cut-off looming, how I was feeling in that moment mattered more than the extra KMs. I chose camp. Save the legs for tomorrow, save the energy for Rwanda. The checkpoints will still be there next year.

Heading towards camp, I’d fallen in with a couple of Scousers. Unfortunately, they were reds. Football loyalties aside, the company was good, and it gave me the extra push I needed. I rolled in with time to spare, and soon the camp started to fill. Riders trickled back one by one, and each arrival was met with cheers.

Whisky appeared, and stories flowed. The best part was swapping tales from the road, who’d braved which climbs, who’d gambled on the biggest detour, comparing scorecards. It was these moments that made the whole thing, the celebration of simply finishing and the laughter over shared misery.

The Tailfin kit got its proper Welsh baptism. Waterproofing tested and capacity stretched. Everything held up. More importantly, I held up. So, is Detours a race or a ride? Honestly, a bit of both. You plan for one, end up with the other, and somewhere in between, you find exactly what you needed.

Next stop, Rwanda. Hotter climbs, bigger mountains, but the same lesson: sometimes the checkpoint isn’t the point. The point is the ride.

More on that to come on Cycling Culture Club.

This feature was produced in partnership with Tailfin, who supplied Phil with free entry and bags to undertake his adventure. Phil was also paid for his time.

Cycling Culture Club is a non-profit however, so we won't consider this an ad, as we take no financial benefit from it.