The Festive 500: Cold Legs, Cracked Tyres, and Christmas Magic

What do you do when something looks doable… but feels impossible?
Over the holidays, I set out to ride 500km in 8 days.
This is the story of spreadsheets, setbacks, cold mornings — and a quiet lesson in resilience.

Every year, Strava runs the “Festive 500.” The rules are simple: ride 500 kilometres (311 miles) between Christmas Eve and New Year’s Eve. Any route. Any pace. Even on a turbo trainer while watching It’s a Wonderful Life on loop.

It’s not the Tour de France. It’s not Paris-Brest-Paris.
But it’s sneaky-hard. Like, deceptively bite-your-own-handlebars hard.

Why? Because on paper, it’s totally doable. Ride 39 miles a day for 8 days. Easy, right?

But winter doesn’t care about your spreadsheet. And neither does your body after Day 3.
There’s the cold. The early sunsets. The fatigue that builds, day after day, until even putting on your gloves feels like a life decision. And let’s not forget… the mechanical surprises.

Over the years, I’ve tried the Festive 500 many times. Sometimes I made it. Sometimes I didn’t.
This is the story of my 2025 attempt.

Day 1 – The Crackening

I had a plan: get ahead early.
Aim high on Day 1, so if things fell apart later (and they always try), I’d have a buffer.

I plotted a 71-mile route. The weather was crisp, the sun was shining, and after some mild distraction involving 3D printing, I finally rolled out… at 11:30am.

The first half was smooth—tailwind, good legs, classic optimism. But then I turned. The tailwind became a headwind. I slowed. The cold sank in. By mile 50, I was empty. I shoved food in like I was trying to bribe my metabolism, but it was too late. At 60 miles, I cracked.

I crawled home up the final hill as dusk fell, fingers numb, vision blurry.
I had done 69 miles… but wondered if I’d already broken myself on Day 1.

Bleak but fast. Winter miles always look easier when you’re standing still.

Day 2 – Surprise Recovery + Christmas Gremlins

Merry Christmas!

I expected to wake up wrecked.
Instead, I felt… okay?

I planned a short loop, 31 miles, ready to cut it short if needed. I left the house feeling awful—freezing, nauseous—but after a while, I warmed up. Then I felt good. Then really good.

I extended the ride. I hit 40 miles. I came home buzzing.

…And discovered my boiler wasn’t working. Half my electronics were dim. Christmas dinner was delayed due to low voltage across the neighbourhood, and I had to call the National Grid like some kind of post-ride wizard of infrastructure.

But hey—I showered eventually. It was a weird day. A good one.

Quantifying Suffering

Yes, I made a spreadsheet. By the end, it could practically forecast my mood.

Not just the distances I’d ridden, but how many miles were left, how many I’d need to ride each day to stay on track, and whether I was ahead or behind.

It might sound a bit over the top, but it actually helped a lot.

The only thing colder than the roads was the logic in this spreadsheet.

Riding 300+ miles across winter days sounds impossible when you think about it all at once.
But having a spreadsheet let me break it down: How many miles do I need to ride today to stay on track?

On days when I pushed a bit further, I could see the numbers shift.
As the daily required rate went down. The challenge got easier.
Watching the spreadsheet update was like watching the pressure lift — not all at once, but gradually.

It became a kind of feedback loop: ride a bit more → make tomorrow easier → feel slightly more in control.

Days 3 & 4 – Grinding On

Day 3: 64 miles. A road closure added a few bonus miles, but the weather was fine and the ride was uneventful. I passed the halfway mark.

Day 4: 51 miles through frost-tipped roads and a National Trust site. Dry, bright, cold.
Nothing remarkable happened, but the quiet miles were stacking up.

87 miles to go.

Day 5 – Tyre Explosion Incident™

I set out aiming to do 50 miles, leaving just 37 for the final day. Perfect plan.

Until mile 5, when my rear tyre exploded.

No pothole. No warning. Just boom. I swapped the inner tube, pumped it back up… and saw it bulging out the sidewall. Torn tyre. Ride over?

I limped home, praying I hadn’t destroy the wheel.
Miraculously, the rim was fine. Even more miraculously, I just so happened to have a spare winter tyre in the right size, make, and model. Plus tubes.

By midday, the bike was fixed. I hadn’t even changed out of my cycling kit. I ate lunch.
Then I headed back out.

I stayed local, in case anything else went wrong. But nothing did.
The ride was joyful. Hills. Sunshine.
I kept going until it started getting dark.

I finished with 51 miles total. Only 36 left.

Day 6 – Return to the Hills

Getting out the door was hard. My legs were heavy, my brain was soup.
The first mile felt like it took an hour.

But I had a thought: flat roads were strategic, flat and boring… but I missed the hills.

So I went off-plan. No route. No spreadsheet. Just my favourite roads, my favourite climbs, riding until the odometer told me I’d done enough.

It was much harder. The hills made it hard to get into a rhythm. But that made it all the more satisfying.

It was a beautiful, brutal, brilliant ride.

I finished early. The spreadsheet saw it coming before I did.

Final Thoughts

So after all I finished with two days to spare. No fanfare. No finish line. Just: “I did it.”

What’s strange is how impossible it had felt before I started. Or even halfway through.
And yet—I made it happen.

And that’s the bit I keep thinking about.
How did I do it?
I think it comes down to resilience.

I realised that resilience isn’t about pretending a thing is not difficult.

It’s about knowing that it is—and still trying anyway.

It’s not optimism. It’s commitment.

Planning, adapting, showing up tired, being unsure but still moving forward.

Even when your legs scream.
Even when your boiler quits on Christmas day.
Even when your tyre explodes.

I didn’t need to believe I would do it.
Just that it was worth trying.

That’s how I did it.
One cold mile at a time.

Davide la Locomotive