A Journey Through Time: Exploring the Nakasendo Trail

Nakasendo had been on my bucket list forever. There’s something irresistibly romantic about tracing the footsteps of travelers from centuries past, strolling along the historic road connecting Edo (modern-day Tokyo) and Kyoto.

The Nakasendo trail, spanning roughly 530 kilometers, was one of the two main roads in Japan during the Edo period (1603-1868). It stretches through a number of prefectures and it's famous for its charming post towns, lush natural scenery, and preserved atmosphere, which makes you fell like you have transported back in time. During Golden Week (holiday at the beginning of May) a few years back, after an exciting exploration of Kyoto and Gifu, tackling the Nakasendo trail became my grand finale. If you love nature, history, and gentle hikes, Nakasendo will feel like pure magic. I walked only a small part of it - the most popular one, but I do believe the less popular parts must be as beautiful!

My journey began in Iwamura, an enchanting village often dubbed "the Machu Picchu of Japan" thanks to its impressive hilltop castle ruins.

Arriving there felt like stepping into a Studio Ghibli movie, especially the last train ride - the orange and yellow colored sunset sky was reflecting on the rice paddies after rain, the air was fresh and besides the sound of the train making its way through this painting-like scenery, it was blissfully quiet.

The one-car train was gliding peacefully as it was getting darker outside and it was just me and two locals sharing this idyllic countryside scene. Well, one was enjoying the scenery and one was deeply asleep. I hope they did not miss their stop.

The reason I was starting my Nakasendo trip here and not closer to the starting point was that, as usual, I left things to the last minute. I booked the only available accommodation last-minute—a traditional wooden guesthouse in the center of the Iwamura village. When I arrived, the elderly lady who managed the house was already waiting for me. She quickly showed me around and then looked at me and stated: "You are hungry!". It was not a question.

To be honest, I was, indeed, quite hungry, so there was no point in arguing with her as she gently ushered me into her tiny car. (Just a note: usually, you should not get into a strangers car, even if it is a lovely old lady). We drove through the narrow streets of the village and two minutes later she safely deposited me at a small but bustling izakaya, probably the only place open around at this hour.

She greeted everyone warmly, introduced me briefly and vanished mysteriously into the night. My table companions—two lively women and a cheerful gentleman, who have been friends since elementary school—started shyly asking questions, but once they found out I speak Japanese, the conversation got going. We laughed, drank sake and beer, and shared delicious local dishes. Before parting, they insisted on paying for my meal, exemplifying countryside hospitality.

Back at the guesthouse, I chatted briefly with another adventurous solo female traveler and after a shower I quickly headed to bed. I had to wake up early the next morning to catch a train so that I can catch the bus to the begging of my hike. Missing this train would mean missing the bus, delaying my day by about 2 hours, which I could not afford. As I felt slightly tipsy from the sake I had with my new friends I went to double check my alarm and quickly drifted off to sleep.

I woke up.. with barely ten minutes to catch my crucial train connection! Somehow I have managed to make a mistake when setting the alarm. I frantically changed out of my pajamas and sprinted through the picturesque streets lined with beautiful wooden Edo-period houses. I managed to snap one shot of the street before dashing to the station. Thankfully, the kind station attendant spotted my desperate run and held the train for a few seconds for me, which is something that usually never happens in Japan. Breathless but victorious, I boarded amidst amused schoolchildren's giggles.

I safely arrived to Nakatsugawa, the gateway town to the Nakasendo trail, which is renowned for its chestnut treats and historic charm. I freshened up at the tourist information center bathroom, and finally looking somehow put together I grabbed a strawberry sandwich and a drink from the convenience store. The weather was perfect, so I enjoyed my breakfast on a bench while waiting to board the bus bound for Magome-juku, my starting point.

Magome-juku is one of the most famous post towns on the Nakasendo route, beautifully preserved with cobblestone streets and traditional wooden buildings dating back hundreds of years. Once home to legendary novelist Shimazaki Toson, it’s incredibly photogenic, with stunning mountain views greeting visitors from the moment they arrive. After grabbing a map at the visitor center (and noting the numerous "Beware of bears" warnings), I set off on the scenic 10-kilometer hike toward Tsumago-juku.

The trail was everything I have imagined it to be—lush forests, gentle hills, occasional shrines along the way and.. lots of "bear bells" to keep wildlife informed of human presence. An unexpected thing was intermittent free Wi-Fi, perfect for sharing moments instantly. I did not make use of it, as the whole point of this trek was to disconnect and enjoy the nature.

Midway between Magome-juku and Tsumago-juku on the Nakasendo Trail, I encountered a charming rest spot: the Ichikokutochi Tateba Chaya. This 250-year-old teahouse, lovingly maintained by local volunteers, offers weary travelers a glimpse into Japan's Edo-period hospitality. 

As I approached, the sight of a late-blooming sakura tree gently shedding its last petals unfolded in front of me.  Seated on a bench outside, I joined an elderly couple who warmly offered me a fresh mini tomato—a simple gesture, but it made me feel so.. glad to be alive and to have set out on this trip. (And yes, I know you should not take food from strangers, even if they are an lovely old couple).

Inside the teahouse, there was free green tea to take for travelers. Sunlight peaked through the wooded walls inside the room, where the interior centered around a traditional irori hearth. I returned outside with a cup of green tea to find the couple still there, now sharing homemade cookies. We exchanged smiles and a few words, savoring the peaceful moment beneath the cherry blossoms.

This brief interlude at the tea house was a heartwarming reminder of the kindness that threads through the journey along the Nakasendo Trail.

The second half of the trail lead me to two beautiful waterfalls. The were hidden a little bit away from the main road, but were so beautiful, you might think they are edited into the video for a moment. What was so amazing about the waterfalls, besides the astonishing scenery, was that it was nice and cool next to them - a natural air conditioner. I wanted to stay to enjoy them longer, but needed to move along.

As I walked along the Nakasendo trail, my mind wandered in every direction—like it finally had room to stretch its legs. I thought about my life in Japan, my career, my future dreams, my relationships, my family, and my health. Then, of course, I had a brief mental detour: What if I get eaten by a bear? I mean, the warning signs were everywhere. But don’t worry—I faithfully rang every single bear bell I passed. No surprise bear attacks on my watch.

There’s something about being surrounded by trees, silence interrupted only by the birds singing and the wind in the trees, and fresh mountain air that clears your head like nothing else. All the usual stress from work? Gone. Instead, I found myself imagining what it must’ve been like to travel this road hundreds of years ago, and how cool it would be to walk the entire Nakasendo one day.

Honestly, this walk wasn’t just good for the legs—it was good for the soul. The kind of stroll where your thoughts roam free and nature gently reminds you that everything’s going to be okay.

Soon after passing a house with beautiful purple wisteria flowers decorating it, I arrived in Tsumago-juku. Renowned as one of Japan’s best-preserved Edo-era towns, Tsumago's wooden facades, lovely souvenir shops, and quiet ambiance were captivating. There were actually quite a few people around, but it did not feel crowded at all at that time. It was tempting to linger, exploring more hidden corners of the city, but daylight urged me forward to Nagiso to make it back home safely on the same day. Only 3.5km left to go.

The last part of the trek was mostly on a road that was winding its way along a side of a hill. I passed a few houses and wondered - how much you must love peace and quiet to live so far away from everything else. Before long, I arrived at Nagiso, another historically significant stop on Nakasendo, and the trail's end for me. With about 20,000 steps logged, my weary feet and empty stomach led me straight to a cozy café opposite Nagiso Station. Here, I had unquestionably the best Japanese curry of my life, savoring every bite as I reflected on the day's adventure.

Boarding the train home, exhausted yet exhilarated, I marveled at the warmth of locals, Japan’s rural beauty, and the simple joy of walking a historic trail. The Nakasendo isn't merely a hike—it's an immersive journey into Japan's past and a heartwarming encounter with genuine hospitality.

Walking the Nakasendo - Gallery