Kusatsu has been a transportation hub for east–west travel on the ancient Tōsandō and Tōkaidō highways connecting the capital of Heian-kyō with the provinces of eastern Japan from the end of the Nara period onwards.

Around 1568, Oda Nobunaga forced Ashikaga Yoshiaki to cede the Kusatsu area, which he viewed as strategically critical to controlling the approaches to Kyoto.

In the early Edo period, the system of post stations on the Nakasendō and Tōkaidō was formalized by the Tokugawa shogunate in 1602.

Coming from Moriyama-juku, the borders of Kusatsu-juku started at the banks of the Kusatsu River and extended to the present-day Miya-chō in Kusatsu.Per the 1843 "東海道宿村大概帳" (Tōkaidō Shukuson Taigaichō) guidebook issued by the Inspector of Highways (道中奉行, Dōchu-būgyō), the town had a population of 2351 in 586 houses, including two honjin, two waki-honjin, and 72 hatago.

In June 1699, the two main players of the Akō incident, Kira Yoshinaka and Asano Naganori stayed at the same honjin but only nine days apart.

Another crisis occurred in 1839, when Shimazu Tadayuki, daimyō of Sadowara Domain died of illness at the Tanaka Shichizaemon Honjin while on sankin-kōtai.

As he had no heir, this placed the domain in imminent danger of attainder, and Tanaka Shichizaemon assisted the Shimazu clan in concealing the death from officials of the Tokugawa shogunate for over two months, claiming that the daimyō was simply resting.

The print depicts a busy scene within the post station itself in front of the open-fronted Yōrō-tei (養老亭) tea house in which many patrons are enjoying Ubagamochi (姥が餅), a sweetened sticky rice cake which was a speciality of Kusatsu-juku.