Due to the lack of studies on the history of the literary circle of the Nikolaev Engineering School, this article is the first to examine its creation and functioning. The aim is to analyze the main forms of activity of the literary circle of this military-educational institution. In order to achieve this goal, data from the annual reports of the Nikolaev Engineering Academy and the school for the academic years 1906—1912 and other pre-revolutionary printed sources were collected. The results obtained show that a positive role in the organisational, library, publishing and methodological assistance to the circle was played by the command of the academy and the school, teaching, administrative and drill staff (N.A. Kryukov, F.I. Zubarev, V.V. Yakovlev, N.N. Polilov, V.F. Naidenov, etc.). This study has expanded the idea of the pedagogical activity of the famous Russian literary scholar, bibliographer, pedagogue F.A. Vitberg, who created the Literary Circle for the Junkers of the Nikolaev Engineering School, revealing for the first time this new page of its life, about the musical creativity of C.A. Cui, who wrote music on the poems of the cadets and successfully combined the composition of musical works with the teaching of military engineering. The names of the pupils of the school who took an active part in its fruitful activity during the mentioned period are established. The beginning of the literary activity of cadet B.V. Zhirkovich, who later connected his fate with literature and became famous as a satirical writer under the pseudonym I.K. Prutkov, is outlined. A brief characteristic of some works published in the “Collection of Literary Circle” No. 1 (St. Petersburg, 1907) and No. 2 (St. Petersburg, 1909) is given. The contents of both issues are presented.