3-Day Nakasendo Trail & Nagano Highlands Journey: Nagoya to Kawagoe

This three-day journey follows a route that most travelers skip entirely: the old Nakasendo trail linking Nagoya to the mountains of central Japan and onward to Kawagoe near Tokyo. The Nakasendo was one of the five great roads of the Edo period, connecting Kyoto and Edo through the interior rather than the coast, and Narai-juku is one of its best-preserved post towns, a strip of wooden merchant houses and inns that once sheltered travelers making the same crossing on foot centuries ago. Walking its main street today feels less like a museum and more like a town that simply kept building in the same style.

From Narai-juku the route continues to Matsumoto, home to one of Japan's oldest surviving original castle keeps, and then into Nagano, the city that hosted the 1998 Winter Olympics and remains a gateway to the Japan Alps. The journey also takes in Togakushi, a mountain area long associated with shugendo, Japan's mountain-ascetic religious tradition, and with a network of shrines that predate most of the Edo-period towns seen earlier in the trip. Moving through these stops in sequence traces a genuine historical corridor rather than a list of unrelated highlights, and the mountain scenery of Nagano prefecture shifts noticeably from Nagoya's urban, industrial character.

The trip ends in Kawagoe, a well-preserved Edo-period merchant town just outside Tokyo known for its clay-walled kurazukuri warehouses, making the three days a genuine coast-to-mountains-to-Tokyo-edge transit rather than a loop back to the starting point. At 72 hours across three days, this suits travelers who want deep, unhurried immersion in rural and small-town Japan, connecting two major cities by a historic inland route instead of the shinkansen.