Many living vertebrates exhibit complex social structures, evidence for the antiquity of which is limited to rare and exceptional fossil finds. Living elephants possess a characteristic social structure that is sex-segregated and multi-tiered, centred around a matriarchal family and solitary or loosely associated groups of adult males. Although the fossil record of Proboscidea is extensive, the origin and evolution of social structure in this clade is virtually unknown. Here, we present imagery and analyses of an extensive late Miocene fossil trackway site from the United Arab Emirates. The site of Mleisa 1 preserves exceptionally long trackways of a herd of at least 13 individuals of varying size transected by that of a single large individual, indicating the presence of both herding and solitary social modes. Trackway stride lengths and resulting body mass estimates indicate that the solitary individual was also the largest and therefore most likely a male. Sexual determination for the herd is equivocal, but the body size profile and number of individuals are commensurate with those of a modern elephant family unit. The Mleisa 1 trackways provide direct evidence for the antiquity of characteristic and complex social structure in Proboscidea.