Abstract This contribution reviews the evidence for terrestrial organisms during the Ordovician (microbial, land plant, fungal, animal) and for the nature of the terrestrial biota. The evidence regarding the origin and early diversification of land plants combines information from both fossils and living organisms. Extant plants can be utilized in: (1) phylogenetic analyses to provide evidence for the nature of the algal–land plant transition and the characteristics of the most basal land plants; (2) evolutionary developmental biology studies of the characters that enabled the invasion of the land; (3) molecular clock analysis to provide evidence regarding timing of the origin and diversification of land plants. We conclude that the Ordovician was a critical period during the terrestrialization of planet Earth that witnessed the transition from a microbial terrestrial biota to one dominated by a vegetation of the most basal land plants.