Hiroshige's print of Tsumago-juku, part of The Sixty-nine Stations of the Kiso Kaidō series

During the Edo period, Tsumago was the forty-second of the sixty-nine post towns, which connected Edo (present-day Tokyo) with Kyoto. Prior to becoming part of the Nakasendō, it was the tenth of eleven stations along the Kisoji, a minor trade route running through the Kiso Valley. As such, it was a relatively prosperous and cosmopolitan town, with an economy based on currency.

In 1968, local residents began an effort to restore historical sites and structures within the town. By 1971, some 20 houses had been restored, and a charter was agreed to the effect that no place in Tsumago should be "sold, hired out, or destroyed". In 1976, the town was designated by the Japanese government as a Nationally Designated Architectural Preservation Site. Despite its historical appearance, however, Tsumago is fully inhabited, though with tourist shops as the town's main business.