The article is devoted to the study of the iconographic program of the series of five tapestries “Four Seasons. Grotesques”, woven, possibly, in Brussels in the 1540s after a carton by an unknown artist. The name of the author of the cartons is unknown, but it is generally accepted in literature that this artist was part of Raphael’s circle. His style is close to Perin del Vaga, or Giulio Romano. There is also still no information about who was the customer for this unusual tapestry series, which is dedicated to the Seasons, but consists of five tapestries. In addition to the extraordinary composition of the series, attention is drawn to the rich grotesque framing of the main subject, located in the center of each tapestry, in the central tondo. Upon thoughtful examination, the viewer notices that all the accompanying figures have their own history, have a special relationship with each other, connected with the main composition in the circle. The more an attentive and interested viewer looks at the numerous figures and details of the images on the huge wall hangings of the series, the more he understands that behind the understandable image of the Seasons there is something much more complex, some kind of deep content, accessible and intended for a few intellectuals who know the codes to this riddle. The basis of the iconographic program is one of the plots from the popular work of the late 15th century — “Hypnoerotomachy of Poliphilus”. However, the deep symbolism of the images goes beyond just a literary work and is associated with the alchemical model of the world, where the four seasons — the four elements — through transmutations and transformations, as a result of struggle and fusion, lead to the appearance of the highest, fifth element — ether, sunlight, which is symbolized by the sun god Apollo. A brief analysis of the iconographic scheme of the series of tapestries “Four Seasons. Grotesques” from the Hermitage collection was undertaken by us for the first time. There is no doubt that many details, allegories and allusions were left beyond the scope of this brief study. There is still much to understand about these undoubtedly outstanding works.