The Usui Pass (碓氷峠) is, without doubt, one of the highlights of the Nakasendo. Most of the hike is spent on mountain trails, deep in nature. There are endless stone relics and reminders of the past as you hike, as well as fantastic views from the top of the pass on a clear day. The starting point, Karuizawa, adds elements of contrast and intrigue to your Nakasendo trip, as the former post town of the Nakasendo has since developed into a town of ostentatious luxury, shopping, and fine dining, where Tokyo’s rich and the famous spend fortunes on second homes to escape the city heat in the summer. Along the whole Nakasendo, there is nothing quite like it. Follow this with the rugged wilderness of the Usui Pass, the quiet post town of Sakamoto Juku, and finally the old railway town of Yokokawa, and you have yourself a very interesting day out.

Beginning in Karuizawa, the hike starts off by going through the former post town of Karuizawa. Now a vibrant, excessively westernized shopping street, Karuizawa’s bakeries and coffee shops give you a chance to grab breakfast before the hike. The path then quickly enters the mountains, climbing up and up through the deep forests of Nagano Prefecture until you reach the top of the Usui Pass. After a local traditional lunch of soba and mochi (or a bento), and a visit to Kumano Kotai Shrine, the hike begins its long descent into Gunma Prefecture. This is the final drop on the Nakasendo before the Kanto Plain. The long downhill goes on and on taking you way into the mountainside of the ancient road before eventually coming out at Sakamoto, the next ancient post town of the Nakasendo. Sakamoto has gorgeous views of Mount Myogi, which looks more like the steep mountains of Laos than the usual granite mountains of Japan. The hike ends at Yokokawa Station. In less than two hours by train, you can arrive in Tokyo, which is why this hike is often used as the final leg of a Nakasendo hiking holiday.

The small town of Yokokawa has limited accommodation, but for those interested, if you do stay another night, there is a wonderful hike along an abandoned railway called the Abt Road alongside the Usui Pass Railway Heritage Park.

You may have noticed that the price of this hike is slightly higher than the other Nakasendo hikes on offer. For transparency, allow me to explain. As local guides in southern Nagano (the Kiso and Ina Valleys), this is slightly too far for us to really be deemed local. As a result, guides travel and accommodation costs have been added into the price.

During the trip, I will provide hot drinks and snacks and you can even try on my own handmade waraji (traditional Japanese straw sandals), which I specialize in making.