Sydney ultra endurance athlete Giles Penfold laces up to run from Bondi to Manly and back in under 21 hours and 14 minutes – the fastest-known-time (FKT) for the coast-hugging 152km route.


My housemate James shakes my shoulder with intent, telling me to wake (the hell) up. I stare at my Garmin in dismay. It’s 11:26pm and I’ve slept through my alarm.

I’ve got 34 minutes until I have a wild crack at setting an FKT on my second 100 mile attempt. The first time, I failed miserably, seriously injuring myself in the process.

‘Yep, awesome start,’ I patronisingly think to myself.

‘At least I’ve got an extra hour of sleep under my belt,’ the optimist rebuts.

Stress and a whole lot of hurry ensue. I chow a bowl of oats down in record time.

James gives me a lift and I arrive at Bondi Beach one minute before midnight.

I set off and can’t help but feel a strange sense of comfort in the darkness, silence, and solitude.


10°C at the start line in Bondi


The task at hand looms over me. My monkey mind does its best to inject fear, reminding me that on my last 160km attempt, I dropped at kilometre 117.

Shaking these self sabotaging thoughts is always part of the fun. A more legitimate ratio sums up my initial mood; 10% daunted, 90% absolutely stoked.


The Out

The first 10km section from Bondi Beach to Watsons Bay flies by as waist-high solar-powered lights dot the cliff tops, acting as my guides through familiar territory, albeit in unfamiliar circumstances.

‘I wonder how I’ll be feeling here on the way back,’ I ponder.

‘Probably not the best,’ I rationalise.

My strategy is simple; remain calm, loose, and floppy at all costs. Shaking my upper body every few kilometres weirdly hits the spot under this tenet, as does the occasional big sigh after a double inhale through the nose.

The mental games are kept at bay as I hug the coastline of Sydney’s east, zigzagging across small beaches and empty suburban streets.

I’m well ahead of my scheduled times; great, but equally problematic seeing as Eddie, my first pacer, isn’t able to meet me at the designated point.

I reckon a solid measure of friendship can be substantiated by your mate agreeing to meet you at 3am to keep you company on some trivial physical feat.

Voice messages flow freely between his phone and mine. Plan B is now for us to meet at Circular Quay, next to the Opera House. Eddie jumps on a rental E-bike and cycles as if he’s in the Tour de France.

I head through the CBD, while Eddie rushes to Circular Quay. Having already passed groups of party-going drunk tourists, I’m long gone, trotting across the iconic Sydney Harbour Bridge. Eddie believes he can ride across the bridge but this idea is quickly brought down to earth. Uber it is.

And so an hour and a half later than planned, we finally coincide at Andersen Park in North Sydney, 42km in. One marathon down, three to go.

Eddie playfully tackles me (his way of saying hello) and I feel a sense of relief as he hands me a ziplock bag full of my race nutrition.


Eddie walking through North Sydney


We trundle on into the night, chatting and weaving our way through Cremorne before entering Sydney Harbour National Park, which protects a number of islands and foreshore areas around the harbour.

This 12km section from Taronga Zoo to the The Spit is spectacular and is an underrated gem in Sydney due to its superb swimming spots and well preserved natural landscapes.

Sixty clicks in, we arrive at The Spit where I have my first sit down and refuel. James and Michael have set up a table with truck loads of food and drinks. They bombard us with questions and smiles.


DIY checkpoint packed with salty foods | Michael Puterflam


I can’t help but feel a bit of imposter syndrome. ‘Do I deserve this?’ subsequently morphs into a genuine appreciation for their help and support.

I gluttonise on fruit, muesli bars, coconut water, and the king of all running foods: pickles (due to their immense saltiness).

After a ten-minute respite we’re in motion again, making for Manly Wharf on stiffening legs. Eddie inadvertently provides a highlight: he has somehow managed to smear bird poo all over his face – good shit, plus a sign of good luck!

By contrast, the sunrise is magic, made more special by having run for six-and-a-half hours.


Sunrise with Manly Wharf in the distance


Again, we meet our crew at the wharf. Eddie’s body has had enough and so I continue on alone, snaking my way around North Head which has scenic views over Sydney Harbour.

Things are going according to plan. I’m an hour ahead of schedule. Cool temps and clear skies means the weather is immaculate. My mindset and body are there.

I reach the halfway point at Manly Beach, greeted by crew and friends.

8.5 hours and 76km done and dusted.

I take another ten minute break here, putting on a fresh shirt, chatting, and eating and drinking. I’m surprised at the amount of people that are here and seem to give a toss.


Friends watch on during the ten-minute break at Manly beach | Michael Puterflam


‘The fun part starts now,’ I think to myself. Time to get back to Bondi in one piece.


The Return

George joins me for the 11km North Head section. His destroyed runners and lanky physique would convince most he’s an avid runner. Looks can be deceiving.

As we roll through Manly Wharf, George and his wrecked calves retire and an old uni friend, Gus, joins me for the next 20km stint.

We keep a steady six minute/km pace and as we chat, it becomes increasingly apparent that without Gus and everyone else helping today, I’d be pretty miserable getting back to Bondi.

The day heats up and we’re saved by crew who hand us luxuries in the form of watermelon and cold soda water. The trail also begins to fill up with tourists and weekend walkers that we brush past.


Running through Sydney Harbour National Park | George Kingston


Soon enough, we pass Taronga Zoo, stopping in a quaint park known as Sirius Cove. Gus has officially run his longest ever distance. Epic!

Here, my parents and Zoe provide equal amounts of support as they do in annoyance (as all good families should). Another ten minute pig out takes place, as my Mum goes into full Mum mode and proceeds to whip out the camera just as I’m leaving.


Ten-minute break at Sirius Cove with Gus, Ingrid, and Ads


Ads joins me for the next chunk and his enthusiasm is off the bloody charts! He’s convinced I’m part fruit loop, part cyborg for wanting to run 150km. I guess it’s somewhat understandable if you haven’t spent much time in and around the trail running community.

My body is feeling the mileage by now.

The fact that I’m constantly running with others means it’s next to impossible to get trapped in my head or overthink things. Distraction is bliss.

Ads and I reach the next checkpoint at Milson Park, 127km in. I’m surprised that some unexpected faces have decided to run the next 20 or so kilometres with me.

I feel like Forrest Gump alongside Matt, Kernow, Sophie, Lydia, and Ads.

We cross the Sydney Harbour Bridge, and I’m again overwhelmed with immense appreciation for those supporting me today.

My body starts to deteriorate though. Not in a catastrophic way but in a lingering heaviness kind of way. Six minute kilometres become damn hard. The engine slows.

We wind our way around the Opera House and the Botanic Gardens. Everyone chats with each other in our group of six, but to me, it somehow feels like twenty people. Not quite sure why.


Running with Lydia and Matt, 125km in


Entering the east, we trundle through a few beaches, and Matt has the audacity to call the route BS, because apparently it’s simply not runnable. My defense comes quicker than I’d like to admit, reminding him that Bondi to Manly is one of the only established routes in the world that hugs the coastline of a major harbour. And Sydney has a pretty damn beautiful harbour.

Then out of nowhere, my old maths teacher ‘Simo’ surprises me 130km in. For context, this guy teaches a sliver about numbers and instead, educates his students how to adopt a hungry mentality that’s applicable to all areas of life. Simo is an influential figure to many, and I’m moved to see him for a few minutes.


Simo-not-a-math-teacher in Rose Bay


The show goes on and Ben joins us whilst Matt retires after a 30km stint (the day after he goes on to run a 72 minute half marathon – you’re welcome mate!).

My physical state continues to decline but unlike other occasions, this doesn’t spill over to oppress my mind.

We traverse The Hermitage Foreshore Walk, a gorgeous 2km trail which I experience through a completely different lens. It’s not often you’re 140km deep and get to pass through an area you know like the back of your hand. Weird stuff.


Passing through the Hermitage Foreshore | Ben Fong


I take my last break at Parsley Bay, known for its old bridge and as a great swimming spot. Matt nearly rips out my jugular for taking too long, also known as not going hard enough. 15km to go.

As the sun leaves us for the day, we take in breathtaking views of the entire harbour from South Head.


The sun sets at South Head

Final Steps

Before I know it, it’s pitch black at 5:45pm and I’m 10km from Bondi.

My knees decide to throw a tantrum and initiate a painful stabbing sensation underneath my patellas. To think I’d finish this thing unscathed…

James joins me and we silently roll through the darkness. I pay homage to the small solar powered lights on the track, reflecting on how much has happened since we last crossed paths.

Surprise surprise, I was right – I don’t feel great.

As expected, these last downhill steps to the finish are filled with suffering. I hobble along, unbalanced.


Hobbling through the last kilometres with James


The realisation that I’m a kilometre away hits me hard. Emotions of pride, happiness, and immense gratitude overrun my system. I tap my legs and thank my body for allowing me to do what it has done.

The eerie silence and nightfall of Bondi Beach welcomes me once more. I put the pedal on the gas and squeeze out a five and half minute kilometre pace, making me laugh.

A dozen or so of my family and friends await in the distance. An indescribable high fills me. I touch the life guard tower in a mix of disbelief, shock, and mostly elation.


Finish line smiles with family and friends


It’s taken 18 hours and 29 minutes to do the 152km out-and-back run, which means a new FKT. A frivolous stat with what I hope has a more meaningful story behind it.

The big takeaway glares me in the face:

Surround yourself with people you care about and that care about you.

The love and support has made this day significantly easier than I anticipated, and one that I’ll never forget.

Matt asks me if I could run back to Manly and then to Bondi, completing 300km. Maybe one day.

A big thanks goes to Salomon Australia, whose generosity and support was greatly appreciated.