The article is devoted to the consideration of the subjects and artistic features of the architectural tiles placed on the Pskov Region’s Orthodox churches built in the 14th—17th centuries. The relevance of the article is determined by the increased interest in the history of the Pskov architectural school, the insufficient study, at the regional level, of medieval religious architecture in general and tile art in particular, which necessitated its in-depth study. The scientific novelty of the work lies in the classification and analogues identification of the subjects of the architectural tiles preserved on the walls of the medieval Orthodox churches in the Pskov Region, which is one of the earliest ancient Russian centers for the production of tiles. The article provides a detailed description of previously unpublished images of tiles from Pskov churches and highlights the peculiarities of their perception. By the nature of the images on the tiles, there are distinguished the following groups: geometric, floristic and ornithomorphic ornament, subject compositions. The most widespread in Pskov was floristic ornament, which includes images of grapes, cornflowers (carnations), flower rosettes, flowerpots with various types of flowers, herbal curls, “Flourishing Heart” and “Tree of Life” patterns, as well as ornithomorphic ornaments with images of peacock, turkey, nightingale and other birds. There is a single geometric triangular ornament on the porch tiles of the narthex of the Theotokos-Nativity Cathedral of the Snetogorsky Monastery (the church of the 14th century is included in the UNESCO World Heritage List, the porch is of the 17th century), and a subject composition of a horseman on the walls of the bell tower of the Peter and Paul Church of the former Sirotkin (Seredkin) Monastery of the 16th century. There are also unique tiles with a centaur on the Church of St. George from Vzvoz of the 15th century (included in the UNESCO World Heritage List). Made by Old Russian masters of tile art, the subjects reflect the Christian polysemous symbolism, the laconicism and generalization of the images, the harmonious composition and coloristics of the tiles. The visual perception of architectural tiles influences people, transmitting, in a symbolic form, the picture of the world, spiritual values and meanings of Russian culture from generation to generation.