
Exploration is the thing I most look forward to when I visit a city, other than seeing friends of course :). It usually takes the form of a long walk that cuts across various neighborhoods, allowing me to get a sense of the place’s vibes and to see how the city is connected. My first time in New York I walked the length of Manhattan, and on a subsequent visit, I crossed the entirety of Brooklyn trying to figure out why people kept moving there. Another important aspect of exploration for me is to make lots of stops as I go, like if I see a cute café, shop, or other detour. Even after living in San Francisco for 5 years I’m still exploring, and one of my favorite walks to do is the Crosstown Trail. It’s an 18 mile urban hike that takes you across the city along it’s diagonal. By doing this and really any long walk you get to see a wide variety of the city and helps you better understand it.
Returning to Japan for my second visit, I wanted to dive deep and explore as much as I could within Tokyo. On my first trip to Japan I purchased a rail pass, which allowed me to go city to city, and hit major tourist hubs in the two weeks I had. This let me see a bunch of the country, but it was mostly surface level. This time the idea was to just wander around Tokyo and try to explore more like I’ve done in other cities. Other than this vague idea of exploration I had no concrete plans for my trip upon arriving in Tokyo. Only after I landed did I write a short list of goals and the one that’s relevant to this post was: “Some dumb transit challenge”. What did that mean? I didn’t really know. On my previous trip with the rail pass in hand I did a day trip to Hokkaido, the northern island, on a whim because it was raining in Tokyo that day. It was 540 miles one way taking only 5 hours on the Shinkansen high speed train. I explored this sleepy town called Hakodate before getting right back on the train and returning. So I wanted to do something in this spirit in addition to my exploration, but nothing really spoke to me until my penultimate night in Tokyo. Inspiration struck at dinner when I told the group my ambition to find something fun & dumb to do on my last full day. That’s when someone mentioned that they knew a person who in high school walked the Yamanote Line loop for a charity event. The Yamanote line is a commuter rail line that goes around central Tokyo and is the busiest commuter line in all of Japan. For the event people walked around the loop taking a picture at each station.

I was immediately hooked since it combines my interests in exploration and transit, but since I had conscripted my friend Justin to participate in whatever adventure was decided on, we needed to both be bought in. The 25 miles of walking and projected high of 85F, with high humidity was daunting. But like I said this needed to be both fun and dumb. On the train ride back from dinner we locked in. It was decided we would wake up early to avoid being in the worst of the heat and we committed to meeting up in 6 short hours in front of Shibuya Station.

It’s fun seeing the Shibuya Scramble area this early, it’s so quiet compared to the insanity of the rest of the day. There was light rain sprinkling but not enough to deter us, and it was expected to stop soon enough anyways. As the last of the pass outs were being woken up, we said bye to the Hachiko statue and set off! 30 Stations to visit, 25 miles of walking, and the looming threat of the midday heat stood ahead of us.
The first few stations went by quickly as we walked North: Harajuku, Yoyogi, then Shinjuku Stations, and just like that one hour down and the rain had even stopped. After a quick pit stop at Family Mart to swap out some damp socks we kept on moving clockwise around the loop. As we passed Shin-Okubo Station I saw the capsule hotel where I stayed on my last trip, which unbeknownst to me at the time was the center of Tokyo’s Koreatown. The next couple of hours of walking were quite pleasant as we began to see more and more areas which you would usually only zip by on the train.

Our first food stop was planned for Otsuka Station, which was our 9th visited station, meaning we were roughly a third of the way done. There was a popular onigiri place nearby but alas it was closed on Sundays :(. We pivoted and headed to McDonalds instead, a tried and true way to get a bunch of calories fast 🙂
The northern portion between Sugamo and Uguisudani Stations was the most quiet section, there weren’t a ton of tourist attractions and it was mostly residential. Definitely a blind spot to most visitors, which makes it even more strange that we saw a tourist couple at Komagome Station that we had also seen at Shinjuku earlier in the day. They also took a picture outside of the station, which made us think they could also have been doing a tour of all the stations, but by train (where’s the fun in that). Maybe they were inspired by a Chris Broad video that had come out recently in which he visited every stop on the Yamanote Line and did one activity at each stop. The only other thing of note in this section was the never ending maze of Love Hotels around the Uguisudani Stations we had to traverse.
By the time we reached Ueno Station we had progressed around the loop enough that we were now heading South. As our 16th visited station, it marked more or less the halfway point of our journey. But with 14 stations to go, and the sun starting to beat down on us, we realized it would be a struggle. We found a Starbucks to camp out in while we psyched ourselves to press on. Next we arrived in Akihabara with a plan: we were gonna camp out in the BIC Camera store to recharge our devices and more importantly stand in an air conditioned building for a bit. We found the Apple showroom and commandeered some of the chargers and planned on sticking around until someone told us to leave. By this point we were absolutely drenched in sweat and no one even attempted to speak to us.
As we continued walking South we were absolutely baking but, we couldn’t complain because only ourselves were to blame for being there in the first place. This was also the point where we realized there had been some conversion error when we estimated the time it would take us to complete and in reality it would take at least 2 more hours than we had planned for. Like a wise man once said: WTF IS A KILOMETER!
Approaching Tokyo Station I had a big brain idea, to take the underground passageways through the station basement, so we could escape the sun for a bit. On the surface, it seemed not a bad idea, but once we delved down into the labyrinth that is Tokyo Station we ended up getting lost and had to backtrack. Oh well, 20 stations down 10 stations to go!

The next stretch between Yurakucho and Shinagawa Station was the most challenging, as we passed the 20 mile mark and hit the peak midday temperature. Shade was hard to come by and I thought to myself maybe we should have gone counter-clockwise instead, next time. We stopped for our second meal break near Tamachi Station and got to see the newest of the stations Takanawa Gateway. Once we passed Osaki Station and turned North we could feel that we were in the home stretch.
3 Stations to go
After passing Gotanda Station we could see the Shibuya Mark City building, which overlooks our final destination, Hachiko Square. The end is near!
2 Stations to go
The neighborhoods around Meguro Station were nice but what’s even nicer is there was an indoor moving sidewalk that led to the Ebisu Station.
1 Station left
Ebisu famously had the In-N-Out pop up in Tokyo last year and is also home to a Verve coffee so it really feels like home. But we couldn’t stay for long, as we took our picture in front of the sign and crossed off the last station. Now all that remained to do was walk the 15 mins to Shibuya and complete the loop.

Our de facto victory lap was navigating the concrete jungle around Shibuya Station on the way to Hachiko Square. While we did this we reflected on what we saw and whether it was worth it? We arrived back to start with an increased appreciation of Tokyo, newly developed blisters, and a horrid watch tan.
Just shy of marathon length, but we got up to 28 miles afterwards getting drinks and dinner lol.


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