The sharp-tailed sandpiper (Calidris acuminata) is a long-distance migrant that travels each year from breeding grounds in the Russian Arctic to nonbreeding areas in Australasia. Most adults migrate rapidly from breeding grounds along a largely inland route through Asia. Here we report on the highly unusual migratory strategy of this species in which some juveniles, but virtually no adults, take a pronounced detour to western Alaska before proceeding on southward migration. We analyzed data from our own studies in this region and published and unpublished observations and specimen records of sharptailed sandpipers from the entire Pacific Basin. Each autumn, sharp-tailed sandpipers began arriving on coastal graminoid meadows and intertidal habitats throughout western Alaska during the last half of August and the last sandpipers departed from southwestern Alaska during October and November. Body mass of birds banded or collected across multiple years and sites in western Alaska (n = 330) increased by an average of 0.57 ± 0.06 g per day between mid-August and late October. Records suggest a small, regular movement of juveniles (and a very few adults) along the Asiatic coast, but we estimate from surveys that a few tens of thousands of juveniles stage in western Alaska each autumn. The distribution of sight and specimen records from the Pacific Basin during autumn suggests strongly age-segregated migration routes, with the principal migration of juveniles crossing central and western Oceania in a possible nonstop trans-Pacific flight from Alaska. This is only the second well-documented case of differential migration among birds that involves different routes for adults and juveniles, and it raises intriguing questions about how and why this system has evolved.