The article attempts to examine the process of creating the image of columns and obelisks in the history of architecture, and in particular to study how ancient prototypes infuenced such monuments in the garden space in Tsarskoe Selo. The first projects of triumphal monuments in Russia date back to the 1720s, under Peter I, but they were not realized. No such monuments were erected during the Baroque period. While, in the 1770s, Catherine II developed her new garden in honor of the victories of the Russian army in the 1768-1774 Russian-Turkish war, rostral columns, an obelisk and Ruin tower pavilion were built. The semantic meaning of obelisks changes from one of the elements of a sacred building in ancient Egypt to compositional accents (detached from Egyptian temple complexes) in squares and circus arenas of ancient Rome. In the 18th-century Russia, they were erected as the monuments of military glory in memory of victories. In the 20th century, obelisks appeared as memorials in squares and on graves of fallen soldiers. Rostral columns, which had appeared in Ancient Greece and Rome, become widespread later. This type of monuments communicates the wide range of symbolic meanings. Other types of monuments are also examined in the article for a more comprehensive historical and artistic contexts. Perhaps, an unknown antique monument served as a prototype of the rostra column on G.-B. Piranesi’s sheets, reminiscent of the Morea column. Searching for prototypes of the monuments of military glory is important for understanding their semantics and the meanings that were implied by their royal sponsor. In the chosen aspect the monuments of classicism have been examined only in a small number of studies.