Unique vertical column structures were constructed for the greening of a structure at the Botanical Garden of Vilnius University, in which a plant cover was formed using the turf rolls of semi-natural meadows that were wrapped on 197 columns, with each column consisting of three equal segments. By evaluating the species composition and the abundance of vegetation in the segments of the columns, we studied how this natural cover changes and what its survival potential is. During the five years of observation, 97 plant species were determined in total. Over time, the initial plant species of fertile soils were mostly replaced by ruderal, nitrophilous, and pioneer plants. Out of the 58 original species, 18 disappeared, while 39 new ones emerged. In the vegetation cover on the north exposition of the building, the original species composition declined faster. The most persistent species were ruderal short-lived Conyza canadensis, Melilotus albus, and Urtica dioica, and long-lived Elytrigia repens. As for vegetation classes, the initial plant communities of the Molinio-Arrhenatheretea elatioris vegetation class were partially replaced by the plant communities of the Koelerio-Corynephoretea canescentis and Artemisietea vulgaris classes; however, unformed plant communities finally became prevalent. All directions, including the north, east, south and west, were equally dominated by semi-shade- and semi-light-loving plant species, together with a less abundant representation of light-loving species. Meanwhile, an unexpected establishment of the light-loving annual Arabidopsis arenosa was observed on the least illuminated north exposition. Likewise, the perennial Festuca pratensis, which is particularly resistant to wintering, emerged and spread on all expositions. The vegetation in the vertical columns was dynamic, and the initial plant species significantly diminished in the five years; however, as new species took place, the columns remained sufficiently covered with a green carpet of plants. This study reveals the benefits of using semi-natural meadow turfs in vertical greening of buildings in the harsh climate of a 5b hardiness zone, which is accompanied by distressing climatic fluctuations during the vegetation season.