To celebrate the 150-year anniversary of railways in Japan, and my own personal achievement of having finally explored and written about all 23 wards of Tokyo, I decide to pay tribute to the city in a meaningful way. I choose to do so by embarking on a journey to walk the entire length of the Yamanote Line, a challenge that will allow me to experience Tokyo in a way that I never have before.

As the early morning sun blazes brightly between the gaps in the skyscrapers, I set out to meet my friend Maki. Though not typically a fan of early starts, today will be a long day that calls for an exception to be made. The Yamanote Line, a loop line encircling central Tokyo, is approximately 34.5 kilometres in length. But on foot, without walking on the tracks, the journey becomes a formidable 44 kilometres – just a little over a marathon’s distance. Thus, the route earns itself a playful portmanteau: the Yamathon.

I meet Maki outside a small cafe in Sumida, and we cross the bridge over into Asakusa. She asks me if she can give up, to which I jokingly reply that it’s a bit early to be considering such a thing. After all, with the Yamanote Line constantly circling the city, it’s always possible to find a train station nearby in case the need to give up arises. We set off from Ueno, the start and end point of our journey. Our first decision is whether to walk clockwise or anti-clockwise. After some deliberation, we opt for the latter, as the prospect of navigating through the eerie streets of Uguisudani at night seems daunting. And so, we set off in the direction of Ikebukuro.

As we approach Nippori, the road runs out and we are forced to venture into the familiar territory of Yanaka Cemetery (still no sign of the ‘snow-protective lifting tool’). While meandering amongst the empty graves, we become momentarily lost, but the distant rumble of a Yamanote Line train eventually guides us back to the tracks. We continue on, making our way through Tabata and eventually reaching Otsuka Station. It is here, three hours into our quest, that our journey takes an unexpected detour in the form of an interesting discovery: the first and only Green Lawson in Tokyo.

The thing that makes this store so unique is that it is fully staffed by digital avatars of Lawson employees, rather than human staff members. As we wander into the store, intrigued by the novelty of it all, we decide to explore further. As we pass by one of the avatars, she greets us with a cheerful “Happy New Year” in Japanese. As Maki chats with the AI about our epic journey along the Yamanote Line and my documenting it in a blog, the clever machine quips that it would be happy to strike a pose for a photograph. It suggests three options: a cheerful “wave,” a universal “peace” sign, or a self-deprecating “loser” sign.

Eager to learn more, I take the opportunity to ask the AI about the philosophy behind Green Lawson. To my surprise, the machine responds in fluent English, explaining that the store aims to reduce food waste, support the local economy, and contribute to world peace.

As we resume our walk, the towering buildings along the route create pockets of shade on the pavement. It’s cold in the shadows, but warm in the sun. Maki explains that there are two words in Japanese that both describe these respective conditions, but I find myself struggling to come up with the antonym for “shade.” This lack of an opposing word begins to bother me, and I consider the possibility that it might be a failing of my memory.

We continue on, passing a large group of people running along the street dressed as rabbits, a nod to the Chinese New Year’s chosen animal. At Ikebukuro, we are treated to the sight of sculptures that litter the streets. As we enter Shin-Okubo, we find ourselves wandering through the bustling streets of Korean Town. And at Shinjuku Station, we are greeted by a television screen that displays words in a mesmerising three-dimensional phenomenon.

Almost five hours into our walk, we arrive at the halfway point of our journey: Harajuku Station. Here, people stand in line, eagerly waiting to purchase tapioca from a street vendor. A little further up the street, we see a similar scene, but with people queueing up along the entire length of a road to buy shoes. In Shibuya, we encounter yet another line, this time composed of people waiting to take a photograph of Hachiko the dog, adorned with a special wreath to mark the New Year.

After hours of constant walking, our legs begin to feel sore. We decide to take a well-deserved break at a small, charming cafe. In contrast to the bustling, three-dimensional imagery of Shinjuku Station, the atmosphere at the cafe is a tranquil, two-dimensional one.

With the night falling and the wind picking up, a chill fills the air as we resume our journey through the darkening city. Despite the challenges presented by the fading light and the increasing cold, we persevere, striding forward on our journey. Close to Meguro Station, we are treated to a beautiful distraction in the form of the Meguro River Cherry Blossoms Promenade, a scenic riverside path lined with cherry trees that are illuminated by beautiful pink lights.

The tranquil scene is a welcome respite from the pain in my calves, and Maki and I take a moment to simply savour the beauty around us.

With weariness setting in, we consider the possibility of giving up, but in the end, we decide that we cannot allow ourselves to quit, for the fear of regret is too great. If we can push through and complete this challenge, we tell ourselves, then we can conquer anything. And so, we push on, determined to see our journey through to the end.

We pass through Shinagawa and the newly built Takanawa Gateway Station, the most recent addition to the Yamanote Line. At 5 p.m., the “Yuyake Koyake” bells ring out from speakers at every intersection, beckoning us to return home. But we do not heed their call, for the end of our journey is nearly in sight. In the distance, I am heartened by the sight of the bright illuminations of Tokyo Tower.

Built from the remains of United States military tanks damaged in the Korean War, Tokyo Tower was designed to mirror the iconic Eiffel Tower in France. However, in a show of competitive spirit, Japan deliberately made its tower 2.6 metres taller, earning it the title of the tallest freestanding tower in the world (a title now held by Tokyo Skytree).

As we near the end of our journey, we are mesmerised by the bright lights of Ginza, Tokyo, Kanda, and Akihabara, all of which are transformed into a neon nirvana at night. It is at this moment that I am struck by the realisation that Japan has not just four, but five seasons – one that is marked not by the changing colours of nature, but by the way in which the country’s cities and towns are transformed by the darkness of night.

After a grueling nine-hour journey that saw us take a total of 55,454 steps, we finally arrive at Ueno Station, exhausted but triumphant. Our legs ache and our feet throb with pain, but the sense of accomplishment helps to outweigh the discomfort. Upon returning to Asakusa, I allow myself the indulgence of an ice-cold beer – the best I’ve ever tasted – as a way to celebrate and relax after our achievement. As Maki and I bask in the afterglow of our journey, the fatigue slowly starts to fade away.