The article’s purpose is to introduce into science a set of sketches of Ukrainian and Jewish cultural heritages’ monuments, accumulated in Danylo Shcherbakivskyi’s personal fund at the scientific archives of the NAS of Ukraine’s Institute of Archeology, as well as to clarify the circumstances of creation of the sketches, to systematize them by their chronology and topography, and to identify a number of objects of church architecture. Based on both the already published information and the epistolary sources found in Kyiv archives, it is established that Mykola Valukynskyi (1886–1950) made the sketches in 1920–1921 in southern Ukraine, Kyivshchyna, Eastern Podillia, and Slobozhanshchyna during his service in the Red Army railway brigades and shortly after his demobilization. It is found out that the artist drew some wooden churches, namely the Church of the Holy Presentation of the Most Holy Theotokos in Beryslav, the Intercession of the Theotokos Church in Fastiv, the Church of Saint Demetrius in the village of Potoky, the Church of the Elevation of the Holy Cross in the village of Sidava, the Church of the Great Martyr Barbara in Olviopol (now Pervomaysk), as well as a sketch of a bell tower at the Church of Saints Cosmas and Damian in the village of Leliaky. Thanks to Danylo Shcherbakivsky’s drawings in a diary of the 1908 expedition to the Podillian Governorate, it is determined, which precisely log cabins of churches (altar, central, or narthex) in Fastiv, Sidava, and Potoky crowned the above-dome crosses painted on both sides of the churches. An emphasis is placed on the value of drawings of Jewish culture’s objects, first of all of typical town buildings (Zhmerynka, Brayiliv), synagogue architecture (Koziatyn), and sheer tombstones (Brayiliv). The achieved results made it possible to outline the range of Mykola Valukynskyi’s interests in a more prominent way and to involve in the scientific context the significant visual sources of folk and sacred arts, which are important both in historical-theoretical, purely scientific, and practical (for example, for designing new churches, chapels, bell towers, or above-dome crosses) planes.