It struck me like a slap across the chops; I had never actually done an adventure on my Jack Jones. Ever. I decided to rectify this at the weekend and caught a train to Lithgow early on Saturday morning. The mission? Cycle via Jenolan and Wombeyan Caves to Mittagong by Sunday night – a 208km journey through the remote wilderness of the Blue Mountains

I’d always been lucky enough to be surrounded by great friends who are equally up for these weekends away, however adventuring on your lonesome presents a number of different challenges which require a different skillset and mental approach to overcome. I was curious as to whether I was capable of surviving just one weekend by myself in the mountains. (The guys from Two Breakfasts & Omafiets are to thank for the inspiration for this adventure.)

I was quietly confident that I’d rattle out the required kilometres no issue, a confidence stemming from the fact I’d cycled 38,000km from London to Sydney in 2010-2012. We’d regularly cycle distances of over 150km in a day, so this should be a breeze!

Oh, how wrong I was. What I’d failed to remember is that it had taken me months to get to that level of fitness (and 2012 is a few years ago now…)

I almost fell at the first hurdle. I was up at 4.45am cycling to Central hell bent on catching the first train to Lithgow, but realised when I got there that track work had rendered the trains out of action on the Blue Mountains line. I managed to blag my bike way onto a replacement bus service and shot off through the city lights of a sleeping Sydney, and into the Blue Mountains – my home for the weekend.

When I finally arrived in Lithgow at 9.45am, I was already buggered but itching to start pedalling. It was nut-shrivellingly cold compared to Sydney, and with the forecast reminding me that temperatures were dropping towards freezing at nighttime, I made a detour via a friendly bottle shop to add a small bottle of cockle-warming whiskey to my already hefty panniers.

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I was finally on the road. After zipping around the Lake Lyell, I veered south towards the Jenolan Caves nestled deep within Jenolan State Forest, the perfect antidote to anyone with a uncontrollable fetish for pine trees. I really can’t get enough of the stuff.

Tarmac soon gave way to dirt paths and fire trail; roads that were emptier than a hermit’s address book, and the cool headwind didn’t feel so cold now that I was slogging it up and over hills determinedly.

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I was soon reminded of how ravenous one becomes when riding a bike. I’d filled the top pockets of my shirt with trail mix for easy access, but no matter how much I ate of it I was unable to kurb my demonic hunger. As I pounded up the endless hills to Jenolan Caves i’d grab a handful and throw it in the direction of my face, and occasionally a nut or a raison would find my mouth, but most would be gone with with headwind.

With only a few google map print-outs and no pedometer, I had no real way of knowing how far I was travelling. My only indicator was a signpost that the first set of caves were 60km from my start point, which i’d need to be at by lunch in order to be on track for a Sunday night finish.

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At 3pm I collapsed into the kiosk at the caves a shadow of my former self. I’d come to the stark realisation that I’d bitten off more than I could chew and that to get to Mittagong in time for the last train on Sunday i’d need to bump into Lance Armstrong’s dealer in the cafe. Unable to score, I gulped down a coffee, threw some more nuts at my face, and continued pedalling.

The ride out of Jenolan Caves is so steep that sherpas would quiver at the sight of it. Slogging up this 11.2% average gradient was a real test, but with light beginning to fade I had to make it to the top – approximately 1,600m – and find some woodland to call home for the evening. The occasional car would pass buy, some drivers giving the thumbs of encouragement, others a bemused stare which roughly translates to: “you’re a idiot”.

I scouted out a discrete spot in the woods for the night, slung up my hammock and changed my clothes. Dusk was swallowed by darkness and a near full moon took over. I realised just how cold it was – a fire was essential for warming my soul whilst re-igniting my hopes for getting to Mittagong in time for work on Monday. I battled for 20 minutes to get her going and finally she caught. A smile returned to my face again. I’m not sure why in retrospect, I’d done only about 65km of 208km and my knees felt like they belonged to a retired downhill skier. I cracked open the whiskey, cooked up some dinner and passed out in my hammock at 8pm.

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I set my alarm 5.30am and weirdly woke 1 minute before it went off. I wolfed down some porridge, and was on the road by 6.15am, enjoying watching the world come to life around me. Nature seemed to put on a private show for me. Kangaroos, foxes, rabbits, wombats and all manner of birds singing songs of encouragement, each cheering me on for the big day ahead – 143km to be precise!

Despite it being somewhat of battle, the riding was absolutely spectacular. A gentle tailwind was my friend for the day as I wormed my way along the Oberon-Colong Stock Route via Mt Werong, gum forests so dense and remote it was almost other worldly. I didn’t see another soul for 6 hours.

Was this the most alone i’d ever been? Surely. I enjoyed the feeling of complete solitude; it was strangely empowering. I felt entirely alive and present in that moment. The master of my own destiny.

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A convoy of weekend 4×4’ers broke the silence and my rare contemplation. The front runner pulled over and wound down the their window. Two of the chirpiest human beings i’ve ever encountered piloted the vehicle, and I felt a surge of heat escape the window and warm my face. The woman had an expression as if she’d just witnessed the second coming of Christ:

“Jesus! What the bloody hell are you doing mate? Do you wanna lift?”

I realised i’d encountered a she-devil.

I felt like a monk trapped in Amsterdam’s red light district; brain-blowing temptation. A mind battle commenced: my sense of pride and somewhat flailing self-determination pitted against a fierce opponent: laziness and comfort.

Through gritted teeth and a twitching smile I declined their offer, and off they roared once again.

I kept pedalling.

I passed through Wombeyan Caves and dropped down to sea-level at Wollondilly, before beginning yet another fierce uphill towards Mittagong. The latter half of day two was my favourite; I’d finally found a rhythm and the clouds had cleared to cast a mystical glow across the valley. It was just me and the mountains and they seemed to want to help me get home. I’d also become impressively accurate with my nut tossing.

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The last hour of the trip was under a full moon, and when i finally rolled into Mittagong just in time for the 18.45 train back to Sydney, I was – with want of a better phrase – completely buggered.

As my entire body began to seize up on the journey back to Sydney, I had some time to reflect on what had been a pretty epic weekend. The ride had been a wonderfully nostalgic experience, spending many hours dreaming of the incredible time Jamie and I had spent riding around the world together. Happy memories. I’d seen a new part of the Blue Mountains whose beauty had tormented and astounded me. I’d put my body through an endurance test, and had passed. Most importantly though, I’d survived and sadistically enjoyed my first solo microadventure.