Since the late Paleozoic, insects and arachnids have diversified in the terrestrial world so spectacularly that they have become unquestionably the most diverse group of organisms to ever inhabit the planet. In fact, this 300 million year interval may appropriately be referred to as the age of arthropods. What is the origin and history of terrestrial arthropods? How is arthropod diversity maintained on land? In this rhetorical context we will discuss (1) the degree to which terrestriality is found in arthropods, (2) the physiological barriers to terrestrialization that arthropod clades confronted, (3) the historical record of arthropod diversity on land based on paleobiological, comparative physiological and zoogeographical evidence, and (4) some tentative answers to the “why” of terrestrial arthropod success. We are providing a geochronologic scope to terrestriality that includes not only the early history of terrestrial arthropods, but also the subsequent expansion of arthropods into major terrestrial habitats.