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NAKASENDOKaruizawa-juku to Usui-toge Pass

When most Japanese hear Karuizawa, they do not picture a post town on the Nakasendo route. Instead, they think of a summer resort or a villa community. In fact, the shopping street at the heart of Old Karuizawa bustled with Japanese seniors, even on a weekday. Karuizawa stands out as an unusual example among former post towns on the Nakasendo, thriving today as a popular tourist destination. After the Edo Period (1603-1868) It gained fame as a highland resort visited by celebrities like John Lennon after foreign missionaries recognized its charm during the Meiji Era (1868-1912).

Tracing the history of this town—now widely known as the epitome of a summer retreat—leads you to Karuizawa-juku, a flourishing post town during the Edo Period. Yet today, few remember this aspect of its past. As you walk toward the edge of the shopping street, lined with trendy cafes and vintage shops, the path quickly narrows and people become sparse. Soon, the noise fades away, and nature surrounds you. Though time passes, the road ahead remains unchanged. Waiting ahead was Usui-toge Pass, famed as one of the toughest spots on the Nakasendo.

Interestingly, more foreigners than Japanese walk this mountain pass today, showing how its hidden charm continues to attract international visitors. For those traveling the Nakasendo toward Tokyo, the quickest driving route to Karuizawa is from Shimosuwa, while public transport requires a detour through Nagano. From there, you rejoin the Nakasendo and cross Usui-toge Pass to enter Gunma Prefecture, tracing two sides of a triangle. Now, let us begin our journey through Karuizawa’s history.

Previous Article: Wada-toge to Shimosuwa-juku — Hiking the Nakasendo’s Most Challenging Stretch

If you come by train, get off at Shinano-Oiwake Station, two stops from Karuizawa Station. It is about a 15 to 20-minute walk to Oiwake-juku, the 20th post town from Edo, modern-day Tokyo, on the Nakasendo. Once a bustling junction with the Hokkoku Kaido, the town features a monument marking the crossroads. Historic sites like the main and secondary inns (honjin and waki-honjin) still stand along the old Nakasendo, making it perfect for a leisurely walk.

Continue one station further to Nakakaruizawa. A short minute from the modern station building brings you to Kutsukake-juku, the 19th post town from Edo. Its contemporary streets have more of a resort feel than a traditional post-town vibe. Traditional buildings stood until the early 20th century, but a major fire in the heart of Kutsukake-juku destroyed much of the old streetscape. Later, the station name changed to Nakakaruizawa, which gradually became the accepted name of the area.

Tracing the old Nakasendo, you will find faint reminders like the site of the secondary inn. A stroll along the Yukawa River offers an enduring view of Mt. Asama, which remains unchanged over time.

Next up is Karuizawa Station—the real starting point for continuing a journey along the historic highway. It’s about a 25-minute walk to the heart of Old Karuizawa, where busy streets bustle with tourists. Compared to the two earlier post towns, it feels on a completely different level. What caused this gap?

The Edo Period’s isolation ended, and rapid modernization took off in the Meiji Era. At the same time, the post station system was abolished, and the post towns swiftly faded. It was during this period that Canadian missionary Alexander Croft Shaw first visited, helping to put Karuizawa on the map as a summer resort.

Shaw visited Karuizawa, captivated by its cool climate and stunning views, and shared its charm through word of mouth. Gradually, artists and business elites built their villas here, turning Karuizawa from a post town into the quintessential summer highland resort. The heart of this transformation was the Old Karuizawa area, where the original post town once stood. Shaw’s villa, known as Shaw House, has been restored, with a chapel located nearby. Open to the public, it is now a popular tourist spot in Old Karuizawa.

Shaw House stands at the eastern edge of Old Karuizawa. Beyond it, the bustling tourist scene fades away, replaced by peaceful quiet. It’s then you realize the Karuizawa Shaw fell for may have been the very landscape right in front of you.

Known as the Samurai Trail, the Nakasendo has gained recognition among Western tourists and is becoming a popular walking tour in Japan. Magome–Tsumago route is the most famous, the Karuizawa route is already drawing foreign visitors as well. Karuizawa is easily accessible—just over an hour from Tokyo by Shinkansen. Yet unlike the more commercialized Magome–Tsumago, it retains a peaceful atmosphere. This is a fantastic route to immerse yourself in nature and contemplate history as you walk.

Related Articles: Magome-juku to Tsumago-juku — Follow the Footsteps of Travelers Past

After visiting Oiwake-juku and Kutsukake-juku in the morning, it was already past noon. We took a taxi for the 2.5-kilometer stretch from Shaw House to Usui-toge Pass. Since there is a road separate from the walking trail, this flexible option is one of the route’s benefits.

We climbed swiftly to around 1,200 meters at the pass where Kumano Kotai Shrine sits. Straddling the border between Nagano and Gunma, this shrine is a rare sight in Japan. Opposite it, a teahouse serves Usui-toge Pass’s specialty, chikara-mochi. A red line in front marks the prefectural boundary. From here, we made our way down to Sakamoto-juku at the foot of the mountain in Gunma Prefecture. With an elevation drop of 750 meters, the 7-kilometer trail takes about three hours to descend.

For the first time, I started a mountain pass from the top, and the experience felt completely different. The narrow trail is well-maintained and easy to follow. Signs along the path explain the historical significance of each spot. Since they are all in Japanese, bring a smartphone for auto-translation and let the details spark your imagination as you walk.

Soon after setting out, I encountered a stone monument inscribed with a waka poem. A nearby sign identified it as Omofuishi. From there, I descended a steep slope and walked on until reaching a clearing marked by another sign—Jinbagahara. In Japanese, the name signifies that this was once the site of a battle.

This long descent holds a remarkable historical story. In 1861, Princess Kazunomiya, sister of Emperor Komei, married the 14th shogun, Tokugawa Iemochi, to ease tensions between the Kyoto court and Edo shogunate. A wedding procession of some 3,000 people traveled along the Nakasendo—a massive scale compared to typical processions of 1,000—making it one of the largest events in the route’s history.

To prevent accidents like falls, a 2km-long detour with a gentler slope—now known as the Kazunomiya Trail—was created. This switchback route halved the climb’s steepness and was completed in just three months through rapid construction.

Stories connected to Princess Kazunomiya’s marriage survive in many locations. At Yabuhara-juku—near Torii-toge Pass—records show she stayed at the main inn. It is said that over 20,000 people, including spectators, gathered there, marking one of the largest gatherings along the route.

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Among the five main Edo-Kyoto routes, the Nakasendo had no river crossings and was seen as more woman-friendly. From the mid-1600s, it became the favored route for imperial and noble princesses’ marriages, earning the nickname, Princess Route. Princess Kazunomiya symbolized this tradition. Still, with many mountain passes, the journey was far from easy.

Nakasendo was also called the backroad. While the Tokaido ran along the Pacific coastal plains as the main route, Nakasendo cut through the inland mountains. At about 530 kilometers and 69 post towns—40 kilometers longer than the Tokaido with 53 towns—it often felt like a longer, winding path.

Looking at Japan’s modernization after the Meiji Era, the area along the Tokaido route became known as the Pacific Belt, a thriving industrial zone where the three major metropolitan areas—Tokyo, Osaka, and Nagoya—formed. The popular tourist Golden Route, which links Tokyo, Hakone, Kyoto, and Osaka, also follows this corridor. The Shinkansen and expressways run along the old Tokaido route, which remains a vital transport artery—so this alignment is no accident. However, when it comes to traveling historic highways, the Nakasendo is the true main route.

Looking back, I left Nagoya and crossed three iconic Nakasendo passes: Magome, Torii, and Wada. After climbing and descending repeatedly, I have now reached the Usui-toge Pass. The challenging terrain is part of its unique story. Because it was the less industrialized back route, the Nakasendo still preserves the landscape people saw in the Edo Period, letting us experience Japan’s abundant nature.

Walking deep in thought, the dense forest suddenly opened through a break in the trees, revealing the landscape below. Known as Nozoki, this viewpoint is a highlight of the descent, offering a clear, straight view of Sakamoto-juku spread out below. On a mountain trail that feels endless, spotting the destination lifts the spirit. At last, the long journey along the Nakasendo is entering its final stretch.

Around two hours had passed since I began walking. I paused often to read the signs, so without those stops, I could have arrived sooner. The gentle descent from the pass kept my steps feeling light and easy. I passed only a few groups on the trail and learned that everyone ahead of me was from Europe, America, or other foreign countries. It was clear to me that this route is quietly gaining popularity among international tourists.

About an hour later, I reached Sakamoto-juku. Turning back, the Usui-toge Pass loomed high above. At 450 meters, Sakamoto-juku sits 800 meters below the pass. Usui-toge pass is the only pass included in the three toughest spots on the Nakasendo. Traveling from Edo to Kyoto means facing this demanding climb from Sakamoto-juku—a striking reminder of the route’s challenges.

Traditional buildings still stand here and there along the 700-meter-long straight road, giving a quite different feel from Karuizawa on the Nagano side of the pass. The site of the honjin is now a private home, but there is a signboard, in Japanese, that shares the story of Princess Kazunomiya’s stay.

Just beyond Sakamoto-juku, on the way to nearby Yokokawa Station, stands the Usui Checkpoint. The original gateposts, doors, and roofing materials survive, a reminder of its historical importance. Yet, they no longer stand in their original place, having been relocated to the site of the former guardhouse. Back then, there was a saying about the strict control of weapons entering Edo and women leaving, and this checkpoint enforced harsh inspections to keep daimyo— feudal lords who regularly traveled between their domains and Edo during sankin kotai—from bringing guns into the city and to prevent their wives and children, held as hostages, from fleeing. The strict checkpoint distinguishes Usui-toge Pass from other passes and adds to its story as one of the toughest stretches along the route.

It is about a few minutes from the checkpoint to Yokokawa Station, the endpoint of this Samurai Trail journey. Starting in Gifu, I crossed three mountain passes, passed through Nagano, and finally arrived in Gunma. From here, it is about a 30-minute train ride to Takasaki Station, where the Shinkansen stops. From there, the route passes through Tokyo Station before heading to Nagoya. On the fastest Shinkansen, the Tokyo–Nagoya trip takes just 90 minutes. Watching the landscape blur past from my seat on the Tokaido Shinkansen, I am reminded of how precious the natural beauty along the Nakasendo truly is.

This journey revealed the rich depth of the Nakasendo. Yet, our trip is only halfway complete—another historic highway awaits; one with a background and story distinct from the Samurai Trail. In Japan, the phrase “kata-mairi” means a one-sided pilgrimage—visiting only one of two temples when both are needed to complete the journey. If we stopped here, our trip would be just that: incomplete. Only by walking both routes will our historic highway journey be whole. So, we arrived at Nagoya Station, ready to set out for our next destination—the Kumano Kodo.

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