Birds that conduct long-distance migrations exhibit varied patterns of consistency in migratory timing and site use. Understanding variation in these traits among populations can help uncover mechanisms driving migratory behaviors and identify potential population threats. Whimbrels (Numenius phaeopus) are long-distance migratory shorebirds with a Holarctic breeding distribution, and recent studies have documented population-specific migrations that vary in duration (short to long) and frequency of stops (none/few to multiple). Factors driving these population-specific differences are unclear. We studied the migration ecology of Whimbrels breeding in Alaska, USA, using satellite transmitters deployed from 2006 to 2010 and tracked through 2015. Whimbrels moved entirely within the Pacific Americas Flyway, and some conducted nonstop flights that exceeded seven days across ~ 8700 km. Birds dispersed across numerous sites throughout the flyway, often using agriculture or aquaculture habitats. Whimbrels generally exhibited fidelity to breeding and non-breeding sites, but typically only exhibited fidelity to staging sites used prior to long, nonstop migratory flights. The duration of migration for Whimbrels at more southern non-breeding locations was longer than for those at more northern non-breeding sites, and birds at more southern sites also terminated southbound migration later and initiated northbound migration earlier than birds at more northern sites. Alaska-breeding Whimbrels exhibited greater variation in migratory behaviors than those in other populations in the species’ range. We attribute this within-population diversity to the extensive breadth of non-breeding distributions (~ 70° latitude across ~ 8600 km), a range that naturally shaped individual responses to unequal migratory demands.