Upstream colonizations from islands to continents have played an important role in two major global bird radiations: the oscine passerines and the pigeons. Here, we investigate insular diversification and upstream dispersal dynamics of pigeons (Columbiformes) within the Indo-Australian Archipelago using a supermatrix fossil-calibrated phylogeny and model-based biogeographical analyses. These analyses show that the islands of Melanesia, now centred on New Guinea and considered separately from Australia, have been a centre of pigeon diversification since the Eocene-Oligocene transition (~34 Mya). Geological reconstructions are concordant in suggesting that arc terranes and continental ribbon fragments that underpin the contemporary Melanesian region might have formed extensive archipelagos for much of the Oligocene and Miocene. These islands are also inferred to have functioned as a net source of pigeon lineages for Asia and especially Australia. Arboreal fruit-eating pigeons have colonized nearby continents on multiple occasions yet show little evidence of subsequent radiation. Insular terrestrial pigeons have been largely unable to colonize Asia, and a single Miocene colonization of Australia preceded an endemic radiation. Upstream dispersal may well be a frequent process in the history of the Indo-Australian Archipelago and surrounds, however ecological and environmental factors likely place strong constraints on its success and evolutionary outcomes.