Tokyo ~ Kyoto (Nakasendo)

Riding the Nakasendō from Tokyo to Kyoto offers a journey through history, following one of Japan’s five major Edo-period highways. Unlike the coastal Tōkaidō, the Nakasendō winds through the mountains, passing preserved post towns, rural landscapes, and historic sites.

The modern route follows a mix of paved roads and old stone paths, with notable highlights including the beautifully preserved towns of Narai-juku, Tsumago-juku, and Magome-juku, where cyclists can experience the atmosphere of Japan’s feudal past. The ride includes mountain passes like Usui Pass and Torii Pass, offering challenging climbs and rewarding views.

With a mix of quiet backroads, scenic valleys, and cultural landmarks, cycling the Nakasendō is an unforgettable way to experience Japan’s history and natural beauty.

Route

This route does a reasonable job of keeping the rider on the smaller more enjoyable “Old Nakasendo” without a huge number of detours to take small segments.

The entire route is paved (none of the old walking Nakasendo is included).

Post towns along the Nakasendo

The post towns along the Nakasendō preserve the atmosphere of Japan’s Edo period, offering visitors a glimpse into historical travel culture. Tsumago and Magome in the Kiso Valley are among the best-preserved, with restored honjin (official inns) and waki-honjin (secondary inns) that once hosted feudal lords. Narai-juku, known as the “halfway town,” boasts one of the longest stretches of Edo-era architecture, featuring narrow streets lined with merchant houses. Many post towns offer local specialties, such as gohei-mochi (grilled rice cakes) and handmade crafts, while providing walking trails that follow the original Nakasendō route through forested landscapes.

Below are post towns that are of interest and worth visiting from East (Tokyo) to West (Kyoto)

Narai-juku

Located in Gifu Narai-Juku is one of the more famous and photographed post towns.

The famous Old Bridge of Kiso is also in Narai-Juku

Tsumago-Juku

The Westernmost post town in Nagano

Magome-juku

Magome-juku is one of the prettier post towns along the Nakasendo and is located in Eastern Gifu Prefecture. The walk between Magome and Tsumago is also quite popular

Samegai-Juku

Samegai-Juku is also well preserved and is located right on the border between Gifu and Shiga prefectures not far from Lake Biwa.

Getting there and away

The Nakasendo is a long historic route so large sections are near railways. The only section that isn’t near a railway is between Saku and Suwa Lake in Nagnao.