Even in its heyday, the Nakasendo trail was never quite as popular as the Tokaido — never quite so developed, and never quite so wealthy. While the Tokaido road hugged the coast, cutting a wider, flatter path on its 514-kilometer journey between Edo (now Tokyo) and Kyoto, the Nakasendo connected the two cities via Japan's mountainous interior, rolling over altogether more rugged terrain.

Little about that relationship has changed since the end of the Edo Period (1603-1868). Today, the corridor through which the old Tokaido road ran is the most heavily traveled part of the country, home to the Tokaido Shinkansen line that connects Tokyo to Yokohama, Nagoya, Kyoto and Osaka; various expressways between those cities; and the endless sprawl of Japanese suburbia. The Nakasendo, though hardly undeveloped, still remains the Tokaido's less-accessible and less-explored cousin.

In Nagano Prefecture's Kiso Valley there is a particularly fine extant portion of the Nakasendo, an easy to walk, well-signposted 8-kilometer route that runs between the two former post towns of Magome and Tsumago. These post towns evolved to cater to the Nakasendo's travelers, and were made rich by the Edo Period policy of sankin-kōtai, under which feudal lords and their families had to commute regularly between their fiefdom and the capital.