The Spirit of the #Festive500

The Spirit of the #Festive500

Some celebrate their ride with sweet treats, others commemorate it with a special edition computer game. Browse the very best of ten years’ worth of entries to our annual Festive 500 Awards.

01 December 2020


With eight days and 500km ahead of you, there’s every chance you’ll encounter the unexpected. Whether you’ve gone off-road or jumped on your tricycle, whether you glided to victory or faltered along the way, share your adventures with us, and enter our annual awards. All entries will be judged by an esteemed panel of Rapha staff and sponsored athletes, and there will be a selection of great prizes up for grabs. To be sure you’re eligible to enter, read our terms and conditions and enter before 10th January 2021.

Entries are now closed

This year's winner will be announced soon.


Over the last eleven years, the #Festive500 has become a family affair. In 2019, 13-year-old Oliver completed the challenge with his dad. Capturing the ride, which they finished in five days, Oliver created a flip book to show some of the views he enjoyed along the way. We were so impressed with his efforts and so crowned him the winner of The Spirit of #Festive500 Awards which carried the ultimate first-place prize of a Canyon Grail bike.

“I found the challenge difficult and I am so grateful to my dad for doing it with me. We had a lot of laughs, and only one puncture.”


Riding the #Festive500 is a tough challenge by anyone’s standards. And so it only seems right to mark the occasion. Youngjoo did this by creating a poster and postcards. Bold, bright colours depict the enjoyment as well as the distances covered over the three days in which he completed the ride.



Taking on the #Festive500 is no small feat. It requires preparation, motivation, and dedication. But when you get on the bike and begin riding, it’s a great space to reminisce on the past season. Anna did just that back in 2019, and she recorded it with an illustration she screen printed.


Paulo Macahilig not only completed the Festive 500 but gave out pan de sal – traditional Phillipine bread rolls – to the people he met along the way in his home region of Aklan. The idea behind his awards entry came from a family of artisans who make woven bags. Inspired by them, he customised a collection of woven wonders to mirror the badges of the Festive 500, scooping 2018's top prize in the process.


@Paulo Macahilig

"I took on the challenge to cover 500 kilometers from December 24 to 31. And to make this effort more meaningful, I decided to give out 500 pieces of bread to random people I meet along the way."


It’s important to remember that riding the Festive 500 should be a bit of fun. This was not lost on game designer Hannah Nicklin, who created a satisfying and strangely addictive Bitsy game to celebrate completing the challenge.

Don’t take our word for it though, play the game for yourself, here.



"Rapha has punctuated my cycling life over the years. My first 100km was ridden as part of a Women's 100, as was my last ride in the UK before I moved abroad. The Rapha riding challenges are simple, but the community around them feels significant."


As anyone who has attempted the Festive 500 will attest, going the distance can become somewhat of an obsession. That said, there are certain life events that come before everything else. Karl Maguire managed just 5.8 kilometres in 2018 but entered the new year with something much more important: a healthy baby born on Christmas Day. His charming letter netted him the epic fail award though, on reflection, sneaking in a few kilometres while shopping for baby supplies was more deserving of a medal.


“The Festive 500 was always going to be an interesting one as our baby’s due date was the 1st of January so my wife wasn’t overly keen. In the end my challenge was drawn to a swift end, spent in hospital awaiting the arrival of my beautiful baby girl instead.”


Win Assakul rode the #Festive500 in 2017 on country roads in South West England. An architect by trade, he chose to sketch out his exploits on this beautifully hand drawn map.



“My favourite thing has to be the winter sunrise. Starting out in the pitch black. spinning through the freezing cold and having the sun slowly creep over the hills to warm your bones was a glorious feeling.”


As industrious in the kitchen as he is on the bike, Gavin Osborn commemorated his #Festive500 with a selection of delicious baked goods. What he didn’t eat to keep him going on the bike, he sent to us.

“While riding, the less robust biscuits did tend to disintegrate having been stuffed into a Camelbak but, with a different taste every day, my nutrition never got dull.”


Riding not just five, but six hundred festive kilometres along Japan’s Pacific coast, SG Parson was riding in search of sanctuary from work and kaze no denwa. The Wind Telephone. What he wrote upon his return is a lovely account of his journey and the legacy of the 2011 tsunami on the region through which he rode. Read more, here.

“I have never met Itaru Sasaki but his cousin’s death has always stuck in my mind. He died in 2010. I only know this because of what Itaru did next.”


From dark memories of hunger knock to the elation of completing the challenge, Gary Dumbill’s animated film is an honest tale of hard-earned miles that saw him scoop second prize in last year’s Spirit of the #Festive500 Awards.

“I've normally got my head down grinding out a good average speed, but with the conditions being a bit sketchy I slowed down and lifted my head up. It turns out the English countryside is actually very pretty, which gave me the idea for an animation.”


Last year’s most playful entry was submitted by Pablo Martínez. Having covered the kilometres on roads in and around Madrid, Pablo decided to celebrate his ride by creating the very first #Festive500 board game.

“The game takes inspiration from the constant ups and downs, emotional and physical, on my rides in the mountains near my home.”

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