The Taganrog Chekhov Drama Theater was established in 1827. The theater was subsidized by the City Council since 1828, and its first director was Alexander Gor. The first group of Russian drama arists was directed by Perovsky and toured around the region, giving performances in Rostov, Novocherkassk, Bahmut. The repertoire consisted mainly of dramas, melodramas and vaudevilles.

Since 1861, Italian opera regularly performed in Taganrog. In 1865 was created a stock company to finance the construction of the new theater building. Forty-five thousand silver rubles of stocks were issued, for the total budget of 55,000 rubles. In 1866, Taganrog established its very own Italian opera in a new opera theater building by the project of the architect Londeron from Odessa. The interiors of the theater were designed after the image of the Milano opera theater La Scala. The repertoire of that time included Giuseppe Verdi, Gioacchino Antonio Rossini, Jacques Offenbach, Vincenzo Bellini, Mikhail Glinka, Pyotr Tchaikovsky and others.

In 1874, the Municipality acquired the theater building by the purchase of its stocks. The newly established theater commission decided to dissolve the Italian opera in 1875 for commercial reasons. One of the Taganrog Italian opera's directors and choirmasters - Gaetano Molla - stayed in Taganrog after the opera theater was closed and contributed to promotion and development of music culture in the city of Taganrog.

Anton Chekhov was in love with theater and literature from his childhood. The first performance that he attended was Offenbach's operette "Elena the Beautiful" onstage Taganrog City Theater on October 4, 1873. Anton was a thirteen years old Gymnasium student, and from that moment on, Chekhov became a great theater lover and spent there virtually all his savings. His favorite seat in the theater was at the back gallery for it was cheap (40 silver kopeeks), and because Gymnasium students needed a special authorisation to go to the theater. The permission was given not often and mostly for the weekends. Sometimes, Anton Chekhov and other fellow students disguised themselves and even wore some makeup, spectacles or a fake beard, trying to fool the regular school staff who checked for unauthorized presence of students.

In 1901, the first movie was shown onstage Taganrog City Theater.

In 1935, during the 75th Anniversary Celebrations of Anton Chekhov, the famous artists of the Moscow Art Theater performed onstage of Taganrog Theater: Olga Knipper, Tarasova, Vishnevskaya, Moskvin and others.

In 1944, the Soviet of People's Commissars of USSR named the Taganrog City Theater after Anton Pavlovich Chekhov.

In 1960, the artists of Taganrog Chekhov Drama Theater performed onstage of the Kremlin Palace of Congress in Moscow within the framework of the centennial celebrations of Anton Chekhov's birthday.

During more than 170 years of its history, the Taganrog Chekhov Drama Theater remains the truly Russian drama theater.