Sychyovka was first mentioned in 1488 as a votchina of a Tver prince Ivan the Young, son of Ivan III. In 1493, it became a palace village (дворцовое село) of Vyazma uyezd. In 1776, Sychyovka was transformed into a town. The name derives from a Russian word sych (сыч, lit. "Little Owl"), which also means "a gloomy person".