Records of Kashiwabara-juku itself date back to the Middle Ages when it was mentioned in the Taiheiki, a historical epic of Japan. A post station was first established in the Kashiwabara-juku area in 646. The Kashiwabara-juku established by Tokugawa Ieyasu in the 17th century was approximately 1.5 km (0.9 mi) from east to west, making it one of the larger post stations along the Nakasendō. Different sources place the number of hatago as either 344 or 457, though either number would be large when compared to other post stations.
In 1996, a study was conducted which showed that over one-fifth of the structures in the Kashiwabara-juku area were built in the either the Edo or Meiji periods. Nowadays, it is known for its mugwort, which is the local specialty. At one point, there were over ten shops that specialized in mugwort products.