Trailwalker 2023 is tomorrow!

How Oxfam Trailwalker 2023 works, why it’s hard, and how so many good people have been making it easier for us.

Alan Jones
6 min readAug 24, 2023
A text message from Oxfam warning me to be prepared for cold temperatures and the chance of some showers. Oh great!
A text message from Oxfam warning us to be prepared for cold temperatures overnight and the chance of some showers. Oh great!

All week my nerves have been bubbling up inside me because my Facebook feed keeps serving me up photos reminding me of moments from the eight previous times going back to 2004 that I’ve attempted to complete 100km of rugged bush track non-stop, in the Oxfam Trailwalker Sydney.

All week the group chat between the four of us in the team and our support crew has been full of details we musn’t forget, equipment we have to find, clothing we need to remember to pack and questions about estimated times between checkpoints, support crew logistics, weather conditions, hydration and food plans, and sleep. Not enough sleep!

It starts tomorrow! And we’re in the first start group at 7am! Yikes!

Happy team members Sam, Maddie, Tony and I just before the start of Trailwalker 2015.
Happy team members Sam, Maddie, Tony and I just before the start of Trailwalker 2015.

There are actually three Trailwalker events on the same weekend, on the same route — the 27km, the 55km and the 100km, but for me, it’s always been the 100km because it’s just so… mad! How mad is Trailwalker? Here’s an easy way to understand what’s involved.

If you live in Sydney, you’ve almost certainly driven past Brooklyn on your way north on the Pacific Highway. You’ll know the two big steel bridges across the river and the steep incline on the freeway leading down to the bridge and back up the other side.

My map app tells me it’s 64km by car to Brooklyn from where I live in Surry Hills, and that it would take me about an hour to drive there, and that’s mostly on a freeway with a 110km/hr speed limit.

The route of the 100km, 55km and 27km Trailwalker events.

Now imagine adding another 36km to that distance and rerouting the journey from that nice, smooth freeway you’ve been imagining driving on and instead, let’s go winding our way through the thick bush you can see from your car, up and down those rugged sandstone cliffs your freeway’s been cut through. It’s so steep in some spots, you’ll have to scramble up boulders and even steel ladders. And instead of driving back to where you live, imagine walking or running the whole way from that Hawkesbury River bridge we started from to Tania Park, on Dobroyd Head, on the northern side of Sydney Harbour.

The track conditions and the distance are only part of the challenge. It’s a team event — you’re not allowed to attempt it solo, so you need to recruit and coordinate a team of 3–6 people and make sure they all check in and check out of each checkpoint together. Training and competing as a team introduces complications as people may have different fitness levels, ambition levels and self-awareness levels!

But it’s also my favourite part of the event, as I learn more about myself and my team mates by putting ourselves in a stressful, uncomfortable situation and working together to get through it as a team.

A younger me posing with a trail sign in training for 2009’s event

You’ve got 48 hours to complete it, and if you don’t stop to sleep and you’re reasonably fit, you should be able to complete it in around 30 hours.

It can be very intimidating but in fact, with a bit of luck, some advice from veterans, and a lot of preparation and training, most people can complete it. Training for our Trailwalker this year began in April and we’ve been gradually increasing the length of the training walks we complete to be able to complete 50km injury-free and blister-free.

The veterans I’ve been training with in our team are my best mate Tony Burrett and an old and close mate Peter Crowe, and the very reassuring thing about having them on the team is they’ve both done it several times before. They know how to get to the finish line in one piece (even if that one piece is several pieces gaffer-taped back together). The newbie on the team is my Forever Girlfriend, Kath O’Shea, and while this is her first Trailwalker, she’s tougher than the rest of us combined, and moves like the wind (she beat me in the 22km Ultra Trail Australia trail run earlier this year by a full 30 minutes!). So I feel like we’re a strong team. None of us are spring chickens, and we may not be fast, but we will be smart (unless we make a dumb mistake of course).

We have the best support crew too — Support Crew Master of Ceremonies David Glover and Support Crew First Officer Tim Lumsdaine have both completed Trailwalker as competitors on several occasions and now use that first-hand experience to be the most caring, thoughtful and efficient support crew a team could ever ask for. They were also joined in supporting us on our longest training walk (7am to 8:30pm) by Tara Forman and Alec Jones, who would be supporting us tomorrow too, if they weren’t in NZ on their very first overseas holiday as a couple (awww!).

Another challenging aspect of Trailwalker is the fund-raising — it’s called the Oxfam Trailwalker because Oxfam Australia runs the event as one of its major fundraising drives each year, and every competitor has to raise a minimum of $500 before they’re allowed across the start line. We’re doing well there — we set ourselves the goal of raising $3,500 as a team and so far we’ve raised $7,727 which is more than twice our goal (but we’ll gratefully accept more donations, it’s not too late, and you get a tax deduction!)

We’ve been supported with donations from so many friends!

So I want to take a moment to thank each of the wonderful people who’ve wanted to make a donation and show me they care about the work Oxfam does and the ways I choose to challenge myself. I feel incredibly lucky to know you and I’m very grateful for my support.

Those people are (in order of donating) Mana, Russell, Alejandro, Miranda, Danin, Roger, Dominic, Siobhan, Sarah, Madeleine, Kieran, Daniel, Oliver, Frederic, Bruno, Tanya, Jude, Rachel, Usman, Kaye, John, Kelsie, Anthony, Annie, Jean-Jacques, Majella, Matt, Paul, Guy, (Another) Alan, Rachel, Mike, Peter, Zac, Garry, (Another) Alan, John, Michelle, Rayn, Luther, Leigh, Charlie, Graham, Jean, Fran, Sacha, Larry, Kayla, Nick, Jeremy, John and several anonymous donors.

Thank you, so much!

You can follow our team’s progress live from 7am tomorrow at and although I’ll be trying to preserve my phone’s battery I will probably post a thing or two to my socials.

Now, I’m going to publish this, finish prep and packing, have a hearty carby dinner and get as much sleep as I can cram before tomorrow’s early start.

I hope you have a great Friday too!



Alan Jones

I’m a coach for founders, partner at M8 Ventures, angel investor. Earlier: founder, early Yahoo product manager, tech reporter. Latest: