Habitats around the Gulf of Mexico (GOM) provide critical resources for Nearctic–Neotropical migratory landbirds, the majority of which travel across or around the GOM every spring and fall as they migrate between temperate breeding grounds in North America and tropical wintering grounds in the Caribbean and Central and South America. At the same time, ecosystems in the GOM are changing rapidly, with unknown consequences for migratory landbird populations, many of which are experiencing population declines. In general, the extent to which events encountered en route limit migratory bird populations is not well understood. At the same time, information from weather surveillance radar, stable isotopes, tracking, eBird, and genetic datasets is increasingly available to address many of the unanswered questions about bird populations that migrate through stopover and airspace habitats in the GOM. We review the state of the science and identify key research needs to understand the impacts of en route events around the GOM region on populations of intercontinental landbird migrants that breed in North America, including: (1) distribution, timing, and habitat associations; (2) habitat characteristics and quality; (3) migratory connectivity; and (4) threats to and current conservation status of airspace and stopover habitats. Finally, we also call for the development of unified and comprehensive long-term monitoring guidelines and international partnerships to advance our understanding of the role of habitats around the GOM in supporting migratory landbird populations moving between temperate breeding grounds and wintering grounds in Mexico, Central and South America, and the Caribbean.