Trees provide a wide variety of ecosystem services to society and form the character of the environment and landscape. The analyses of tree populations and their resistance to changing conditions related to climate change typically focus on urban tree communities or forest trees. Similar studies on non-forest trees in the open landscape are largely missing; even the evidence on tree species abundance and distribution is sporadic. The article aims to expand the current evidence by a large-scale study on roadside trees in the Czech Republic. Using an extensive dataset that covers 91.2% of the total tree population along roads in nine NUTS3 regions, we assess the state and observed practices in selecting tree genera for roadside planting and discuss the implications for sustainable tree planning and management. Our survey documented 133,169 tree individuals belonging to 116 species and 40 genera. The results show that 75% of the total roadside plantings along second-class motorways and first-class roads are represented by seven main genera of deciduous trees (Acer, Fraxinus, Tilia, Malus, Betula, Populus, and Quercus), the distribution of which is similar across most Czech regions. New plantings have shifted only a little from the original species distribution. Traditional roadside species are becoming a more popular choice among new plantings, and the effort not to let the invasive trees outgrow into the mature stage is apparent. Most of the original and newly planted species are relatively suitable for emerging risks related to climate change. To achieve more sustainable patterns in roadside tree species composition in the future, especially the susceptibility of some commonly planted roadside tree species to emerging pests and diseases (e.g., Fraxinus excelsior) and to unfavorable site conditions typical for roadside tree stands (Tilia cordata) is of relevance to tree managers. The relative abundance of tree genera was proven to be similar in most studied regions, which makes the recommendations equally relevant for roadside tree managers across the country.