The article discusses the details of A. Chekhov’s visit to the Kaluga governorate, which influenced some of his later short stories. There is a wooden house in Kaluga. Built on a stone basement, it overlooked the boulevard and once belonged to the parents of Mikhail Mikhaylovich Chekhov (who resided in Moscow at the time), a cousin of Anton Pavlovich Chekhov and his active correspondent. The latter even had plans to visit his Kaluga relatives. Sadly, this never happened. But the writer’s brother, Mikhail Pavlovich Chekhov, worked as a tax inspector in the town on Aleksin, an administrative hub in the Tula governorate, resulting in Chekhov’s family visiting the town’s environs in 1891 and staying on the state Bogimovo in the Tarusa district of the Kaluga governorate, which belonged to a landowner E. Bylim-Kolosovsky. It was there that Chekhov was working on his novella The Duel [Duеl] and the book Sakhalin Island [Ostrov Sakhalin]. A spectacular view of the nearby Dankovo, whose purchase Chekhov contemplated for a while, was recreated in his short story The House with the Mezzanine [Dom s mezoninom].