Equipped with a bike my little brother would approve of, and enough warm and weatherproof gear to survive a snowstorm, I began my two day cycling challenge. Although I like walking, skiing and playing soccer, I generally avoid cycling. Cycling Nakasendo’s expert guide had convinced me that this route made jumping on a bike worth it, and, much to my surprise, he was right!
I left Tokyo on the Friday night, headed for Nagoya. The next morning, after a huge breakfast and lugging two giant bags filled with disassembled bikes, we jumped on the train headed for the mountains. It was a surprisingly beautiful day, warm and clear. The train ride passed quickly. It took less than an hour for both bikes to be put back together for the journey ahead. The one I borrowed required assembly, but the other one was a regular folding one, the kind you’d expect to see on a bike track, not halfway up a mountain.


Our first stop was a lovely little shop. We ate Kuri-kinton, a small and round baked sweet made from chestnut. It was about 10:30 and I was ready to test my strength on the first slope. It was definitely a test. I found myself walking up a winding hillside within about half an hour. I decided that maybe the next one would be easier, that by then I’d get used to changing gears in a timely way and might have more luck staying in the saddle. As I mentioned earlier, I prefer walking to riding, so I quite enjoyed pushing the bike uphill, it gave me more time to appreciate the stunning autumn foliage.
Although the scenery was amazing throughout the ride, one of my first clear memories is looking down towards a valley with a large red bridge. There were little houses and fields either side of the road that I was cycling on, and the hills either side of the bridge were forested. The green, gold and red in the distance contrasted well with the muted browns and greys of the village streets. There was a large building with something like steam floating upward above it, so I assumed it was an onsen. It was a nice downhill moment that let me catch my breath and get ready for more climbing.
After a fair bit more riding I felt pretty exhausted and we came to a rather long climb. The destination was a surprising reward. Magome was full of lovely old wooden buildings either side of cobble-stoned streets. With so many people sightseeing that we just had to walk, I saw maples and water wheels, giant carp in tiny ponds and snow-capped mountains in the distance. I ate mountain chestnuts and chestnut ice-cream. And one of my favourite foods, oyaki! A bit like pork buns but slightly flatter and doughier and filled with many different things. I chose a pumpkin one, and an eggplant one. As with everything I ate on this trip they were delicious, and gave me the energy for the next leg.
Or so I thought. I had used up a lot of energy just getting to Magome, and maybe because of that, we had to make an unexpected rest stop when we had barely started towards Tsumago. It was later than expected when we arrived, and the light was mellowing. Tsumago had much to offer, the narrow streets were filled with people and lined with flame-coloured trees. A performer was dressed in a traditional way and happened to be playing music as we passed. I could have happily spent the afternoon there taking photos had we not made a different goal. We were not yet halfway towards our planned destination and I knew that if I didn’t keep moving then I would not make it.


The next hour or so was steady riding while the sun sank. The tawny light made every temple and mountain shine a little more, but it was taking me all that I had to keep pedalling and I took few photos. It wasn’t even cold until after we stopped and it had become dark. I was not sure how much further I could ride. There were about 20 kilometres left, I think, but by uncanny coincidence, as I set off again in darkness dreaming of Kiso-fukushima where food, a warm bath and sleep were waiting for me, my tyre was suddenly punctured. We walked the bikes back to the nearest station. I felt sheer relief at my unbelievable luck, having swapped a daunting ride for a five-minute walk. I stood by and held things while the two bikes were disassembled before my eyes. This was done so fast that we made it onto the train and to our accommodation in time to get clean before dinner. Tsutaya’s food was impressively good, better than at other ryokans I’ve visited. Unsurprisingly, I slept very well.
We started about the same time on the second day, after a relaxing morning where we’d decided on a modified route and I’d watched my tyre being expertly repaired and the bikes reassembled. I had been so slow uphill, despite having the much better bike, that our new route avoided many of the bigger slopes. Even the original plan for Day Two was largely downhill so despite fatigue from yesterday’s ride, I very much wanted to keep going for as long as possible and felt confident that I could make it. After visiting an ancient border control, we came to the halfway point between Tokyo and Kyoto. Luckily for me, because I was already struggling, we discovered that my bike’s gears could use a bit of tweaking, so that let me have a bit of a rest. While yesterday much of the riding was in villages, today it felt more remote. Wide river beds filled with boulders created by volcanoes and occasional glimpses of snow-capped peaks made it refreshingly different.
I get scared riding on the road with cars roaring up beside me and they hadn’t bothered me much today since we were taking many back streets on our modified path. By the time we reached Yabuhara Station, I wanted to try to stay away from the traffic and head for the hills, despite expecting that it could take me as long as an extra few hours. We came across the old route again, the real Nakasendo, and rang the ancient-looking bear bell to keep ourselves safe from any wildlife that might be listening. We even yelled more often as we wound upwards, away from the safety of sealed roads. “Grrrrr”, a low and unexpected noise in the forest to our right startled both of us enough to abandon the remote route. In the moment we heard it we wondered if it was a bear and that was enough to send us heading downhill very quickly. I overtook the folding bike in my haste to get away. As I came back uphill to find out what happened to the little bike, we convinced ourselves that it was more likely to have been a wild boar, if anything. That didn’t stop us from returning to the discomfort of a tunnel full of traffic to get to Narai.


Narai was an absolute highlight. By itself, it is a reason to ride this route. I was delighted to come out of the horrible tunnel and discover this little town. We took time to wander past each building, from the temple down at the mountain end, to the border control building at the other. We stopped for food and to buy souvenirs. The meal was perfect, warm soupy noodles with chicken and mountain vegetables, plus sweets made from rice, soy sauce, miso and walnuts. Friendly hosts made the little wooden buildings all the more welcoming. It goes to show Cycling Nakasendo’s generosity, that not only did he plan and guide the trip, provide the bikes and the history lesson, but he also bought me a furoshiki as a lovely way to remind me of this journey to Narai. I love these cloth wrappings and I have collected a few now to help me remember just how lucky I have been in my time here in Japan.
I wanted to be home by five so we flew downhill. Back on real roads, fear drove my legs to keep pushing me past waterfalls and crimson hillsides as the sun dropped lower. I skipped past highlights, a rare glance back to see a golden spire glint in the distance. As we headed towards the station and our train back to Tokyo, some more unexpected and spectacular views were waiting for me. The first was simply an aeroplane vapour trail against a pink and purple sunset. The entire sky was lit up and the contrast of the wispy, disappearing trail set it off very well. The second one was seeing Hakuba in the distance. Hakuba is the mountain where I tried to learn to snowboard, and it doesn’t look a bit like Mt Fuji. It’s an interesting shape and one of the first in the area to get decent snow. Seeing it, lightly dusted with snow and glorious against the deepening sky, is one of the many memories I’ll treasure from this trip.
In summary, it’s not such an easy ride but it is a beautiful one. I still don’t like riding very much, but I absolutely think that it’s the best way to get a feel for the sheer distances travelled and terrain covered by the people who lived in ancient Japan. My account here is a brief and personal one, and I have left out historical information because it is given appropriate depth elsewhere in this blog. Yet, the interesting history behind this amazing route is what sets it apart from other rides. Thank you for the amazing opportunity to ride a small way along it and I hope to do it all again someday.
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