Nakasendo highway officially starts from Nihonbashi just as others major highways such as Tokaido Highway. Sugamo area used to be the first stop of Nakasendo, Itabashi. Actually most of the old travellers who set foot on Nakasendo Route started the journey from Itabashi. Former Itabashi-stop area used to be thus very bustling place of Edo town.

After passing Itabashi (currently Sugamo area), traveller took the road parallel to current Takasaki Line. It passes major historical towns in Saitama prefectures such as Urawa, Omiya, currently part of huge city Saitama. In Tochigi prefecture, the road stops at Takasaki known by the Huge Kannon Statue. The road turns westward and directs toward Karuizawa by passing Kyu Usui Pass. After passing some stations the travelers faced another hard part, Wada Pass. After passing Wada Pass the traveller enters the Kiso Valley parts of Nakasendo, having lots of highlights such as Narai, Tsumago, Magome. From Oi stop the highway turns to hillside trails reaching to Mitake. After Mitake, the highway runs close to current Tokaido line and joins the Tokaido at 68th stop Kusatsu and 69th stop Otsu. From Otsu the road shares the route with Tokaido and ends with Sanjo-Ohashi Bridge of Kyoto.