Kakegawa-juku (掛川宿 Kakegawa-juku?) was the twenty-sixth of the fifty-three stations of the Tōkaidō. It is located in what is now the city of Kakegawa, Shizuoka Prefecture, Japan.
Kakegawa-juku was originally the castle town of Kakegawa Castle. It was famous because Yamauchi Kazutoyo rebuilt the area and lived there himself.
It also served as a post station along a salt road that ran through Shinano Province between the modern-day cities of Makinohara and Hamamatsu.
The classic ukiyoe print by Ando Hiroshige (Hoeido edition) from 1831-1834 depicts travelers crossing a trestle-bridge. An old couple is struggling against a strong wind, followed by a boy making a mocking gesture; another boy is watching a kite up in the air. In the background, peasants are planting rice and in the distance, Mount Akiba is shown in the mists.