There were several experiences in Chekhov's own life that are said to have directly inspired his writing of The Cherry Orchard. When Chekhov was sixteen, his mother went into debt after being cheated by some builders she had hired to construct a small house. A former lodger, Gabriel Selivanov, offered to help her financially, but secretly bought the house for himself. At approximately the same time, Chekov's childhood home in Taganrog was sold to pay off its mortgage. These financial and domestic upheavals imprinted themselves deeply on his memory and would reappear in the action of The Cherry Orchard.
Later in his life, living on a country estate outside Moscow, Chekhov developed an interest in gardening and planted his own cherry orchard. After relocating to Yalta due to his poor health, Chekhov was devastated to learn that the buyer of his former estate had cut down most of the orchard. Returning on one trip to his childhood haunts in Taganrog, he was further horrified by the devastating effects of industrial deforestation. It was in those woodlands and the forests of his holidays in Ukraine that he had first nurtured his ecological passion (this passion is reflected in the character of Dr. Astrov, from his earlier play Uncle Vanya, whose love of the forests is his only peace). A lovely and locally famous cherry orchard stood on the farm of family friends where he spent childhood vacations, and in his early short story "Steppe", Chekhov depicts a young boy crossing the Ukraine amidst fields of cherry blossoms. Finally, the first inklings of the genesis for the play that would be his last came in a terse notebook entry of 1897: "cherry orchard". Today, Chekhov's Yalta garden survives alongside The Cherry Orchard as a monument to a man whose feeling for trees equaled his feeling for theatre. Indeed, trees are often unspoken, symbolic heroes and victims of his stories and plays; so much so that Chekhov is often singled out as Europe's first ecological author.
Chekhov wrote The Cherry Orchard over the course of several years, alternating between periods of lighthearted giddiness and despondent frustration which he considered as bordering upon sloth (in a letter, he wrote, "Every sentence I write strikes me as good for nothing.") Throughout this time he was also further inhibited by his chronic tuberculosis. Guarded by nature, Chekhov seemed overly secretive about all facets of the work, including even the title. As late as the Summer of 1902 he still had not shared anything about the play with anyone in his immediate family or the Art Theatre. It was only to comfort his wife Olga Knipper, who was recovering from a miscarriage, that he finally let her in on the play's title, whispering it to her despite the fact that the two were alone. Chekhov was apparently delighted with the very sound of the title, and enjoyed the same sense of triumph months later when he finally revealed it to Stanislavski. By October 1903 the play was finished and sent to the Moscow Art Theater. Three weeks later Chekhov arrived at rehearsals in what would be a futile attempt to curb all the "weepiness" from the play which Stanislavski had developed. The author apparently also snickered when, during rehearsals, the word "orchard" was replaced with the more practical "plantation", feeling that with that word he had perfectly and symbolically captured the impracticality of an entire way of life.
Although critics at the time were divided in their response to the play, the debut of The Cherry Orchard by the Moscow Art Theatre on 17 January 1904 (Chekhov's birthday) was a resounding theatrical success and the play was almost immediately presented in many of the important provincial cities. This success was not confined only to Russia, as the play was soon seen abroad with great acclaim as well. Shortly after the play's debut, Chekhov departed for Germany due to his worsening health, and by July 1904 he was dead.