The purpose of the article is to study the poem «The Ancient Night of the Universe, or the Wandering Blind» by Semyon Bobrov from the viewpoint of the doctrine belonged to Russian Freemasonry of the 18th –early 19th centuries. It is based on a combinationof mystical, esoteric, Christian (Orthodox) and en-lightening ideas which allowed this movement to organically fit into the socio-cultural context of the pre-romantic epoch. The analysis of the poem as a philo-sophical, allegorical and esoteric text, in turn, has revealed Russian Freema-sonry’s specificity consisted in the close interaction of various religious, philo-sophical and ethical systems. The special eclecticism of S. Bobrov’s thinking is reflected in the onto-logical, epistemological and axiological problems of the poem and expressed at all levels of the poetic text such as ideological-thematic, figurative, composi-tional and poetological ones. «Dreamy mysticism», consonant with the pre-romantic worldview, creates a general atmosphere of mystery in thepoem and serves as the basis for the image formation of Nesham, the main character, as well as a system of symbols (an eye, a ray, a circle, a temple, a mirror, an oil lamp, etc.). Moreover, S. Bobrov builds the poem structure according to the cat-egories and principles of esoteric thinking like universal correspondences, liv-ing nature (the world as a «chain of being»), mediation and imagination, trans-mutation and concordance. At the same time, a special place in the poem is occupied by the ideas of inner freedom and morality, mercy and compassion, which testifies to the poet’s closeness to Orthodox culture. S. Bobrov’s human-istic orientation, special interest to the category of intellect and attention to epistemological problems testify an «enlightenment» trace in the poet’s worldview. Thereby, the combination of heterogeneous religious, philosophical and cultural concepts in S. Bobrov’s work can be explained by the poet’s close-ness to Russian masons of the 18th –early 19th centuries.