Technological and methodological advances in biogeography, phylogenetics, and bioinformatics during the past couple of decades provide greatly enhanced insights into the evolutionary history of birds in space and time. Molecular data, especially next-generation DNA sequencing, have produced a revolution in reconstructing the phylogenetic history of lineages. These advances shed a new light on the mode, tempo, and spatial context of differentiation processes that shaped the composition and structure of extant forest bird communities of temperate forests of the Northern Hemisphere. This paper offers a framework for understanding this history based on analytical tools that allow us to decipher the imprint of changes in the geographic configuration of land masses and in climates since the Mesozoic, with a focus on the temperate-tropical flyways that connect the massive forest blocks of the Northern to those of the Southern Hemispheres. Differentiation of most extant bird lineages and species has been shown to have begun in a deeper past than formerly thought, although recent analyses from molecular phylogenies also support the much-debated Late Pleistocene model of speciation. Geographical connections between tropical and temperate realms make north-south flyways important drivers of differentiation for many lineages. The histories of differentiation and colonisation of clades, including both resident and long-distance migrants, are discussed in relation to two alternative theories, the ‘southern home theory’ and the ‘northern home theory’. The region-specific characters of the bird faunas and differences between the main temperate forest blocks of the Northern Hemisphere are discussed in light of the hypotheses concerning dispersal processes related with geographical configuration of land masses. Differential dispersal-colonisation rates from tropical regions and subsequent diversification in temperate regions (and vice versa) are also considered. The causes of the observed decline in diversification rates during the Pleistocene are examined from phylogenetic reconstructions of various clades.