This small, generally inconspicuous flycatcher is best known for its plaintive pee-ah-wee song heard through much of the summer in wooded habitats of the eastern United States and into southern Canada. This species spends much of its time in the forest canopy and builds a small nest on a horizontal branch up to 22 m above the ground. The small cup is covered with lichens, producing an inconspicuous nest that may appear very much like a knot on the branch. As a result of its inaccessible and cryptic nest, only recently has this widespread species' reproductive biology been studied in detail.
One of the last spring migrants to return from its overwintering range in South America, the Eastern Wood-Pewee breeds in virtually every type of wooded habitat in the East, from urban forest patches, woodlots in agricultural areas, and orchards, to savannas, riparian forests, and extensive tracts of mature forest. Although it generally inhabits deciduous forest, it also breeds in open pine woodlands (especially in the South) and mixed hardwood-conifer forests of the North.
Although it remains common in most of its range, Eastern Wood-Pewee breeding populations have declined steadily and significantly throughout its range over the last 50 years. Like other Nearctic–Neotropical migrant species, loss and degradation of overwintering habitat in South America and stopover habitat in Central and South America may contribute to population declines; however, populations also experience habitat degradation in North America. Other negative impacts on the species may include heavy browsing of forests by White-tailed Deer (Odocoileus virginianus), which reduces subcanopy foraging habitat, and use of insecticides which may be responsible for widespread impacts on arthropod populations and insectivorous birds.
Highly similar in appearance to the Western Wood-Pewee (Contopus sordidulus), these two species are best separated by their distinctive songs and breeding distributions. Where the breeding ranges of these species have recently met in the Great Plains in western Nebraska, hybridization has been reported. Visual similarities between Eastern and Western wood-pewees, as well as the Tropical Pewee (Contopus cinereus), have made made it challenging to define overwintering ranges.