Unlike the coastal Tōkaidō, the Nakasendō traveled inland, hence its name, which can be translated as "road through the central mountains" (as opposed to the Tōkaidō, which roughly meant "road near the eastern sea"). Because it was such a well-developed road, many famous persons, including the haiku master Matsuo Bashō, traveled the road. Many people, including women, preferred traveling along the Nakasendō because it did not require travelers to ford any rivers.
In the early years of the Edo period, many political, legal, cultural and intellectual changes took place. Among them was the rejuvenation of Japan's thousand-year-old highway system. Five roads were formally nominated as official routes for the use of the shogun and the other daimyo and to provide the Tokugawa shogunate with the communications network that it needed to stabilize and rule the country. One of these five roads was the Nakasendō, which stretched from Edo, from where the shogun wielded the real power, through the central mountain ranges of Honshū and on to Kyoto.
Until the establishment of these formal trade routes, many shorter routes had existed, connecting towns over various distances. One such route was the Kisoji, which had all eleven post towns become part of the Nakasendō (from Niekawa-juku to Magome-juku). Prior to the Edo period, the route had been called both Sandō (山道) and Tōsandō (東山道). During the Edo Period, the name was changed to Nakasendō, though it was written as both 中山道 and 中仙道, but the Tokugawa Shogunate established 中山道 as the official name in 1716.
Though there has been much modern development along the Nakasendō, a few stretches remain in its original form, while others have been restored in more recent decades. The most well-known section lies in the Kiso Valley, between Tsumago-juku in Nagano Prefecture and Magome-juku in Gifu Prefecture. The area was first made famous by the early 20th-century writer Shimazaki Tōson, who chronicled the effects of the Meiji Restoration on the valley in his landmark novel Yoake Mae ("Before the Dawn"). This eight-kilometer section of the Nakasendō can still be travelled along comfortably by foot, and both Tsumago-juku and Magome-juku have preserved and restored the traditional architecture. The walk between the historical post towns requires two to three hours to walk, with forests, restored paving and fine views of waterfalls along the way.
Although much of the Nakasendō no longer exists in its historic form, its route is now roughly followed by modern roads. In order, they are: