Range limits and secondary contact zones often occur at ecotones between major associations of habitat and climate. Therefore, understanding processes that limit sympatry between species in such areas provides an important framework for testing biogeographic and evolutionary hypotheses. Theoretical and empirical work has shown that the evolution of species borders is influenced by a complexity of factors, including gene flow from central to peripheral populations and the ability of species to adapt locally to environmental conditions. However, few studies have used bioclimatic models, combined with molecular and morphological data, to predict geographic range limits in the context of gene flow across a secondary contact zone. In this study, I applied these methods to test specific hypotheses about barriers to sympatry between closely related species where they approach and contact each other. Specifically, I examined the importance of historical isolation, local adaptation, and symmetry of gene flow in limiting sympatry and range expansion of ecologically distinct species across environmental gradients. Molecular (mitochondrial DNA, allozymes), morphological, and bioclimatic data were obtained for two avian sibling species (Baeolophus inornatus and B. ridgwayi) that exist in recent, narrow secondary contact in northern California. These species are broadly allopatric and occupy rangewide associations of oak and pinyon-juniper woodlands, respectively, although B. inornatus also inhabits mixed or juniper woodlands locally. Patterns of molecular variation generally were congruent with morphological and bioclimatic data, and support prior evidence for a history of isolation, adaptation, and divergence in distinctive, species-specific vegetation-climate associations. However, molecular and morphological clines fall east of the limit of oaks, and individuals of B. inornatus in this juniper-associated contact zone experience bioclimates that are more similar to B. ridgwayi than to B. inornatus in oak habitat. Thus, B. inornatus is able to adapt and expand locally into the range of its close relative, but not vice versa. These data support the hypothesis that gene flow is asymmetrical where peripheral populations meet at range boundaries. Physiological differences between species may play an important role in influencing these patterns. Empirical studies that highlight the importance of local adaptation and patterns of gene flow in which closely related species contact across ecotones are central to understanding limits on geographic ranges, sympatry, and introgression—a cornerstone of biogeographic and speciation theory.