We studied the timing of reproductive maturity of cherry fruit fly, Rhagoletis cingulata (Loew), a key pest of sweet and tart cherries in the eastern United States. To determine when cherry fruit fly females become reproductively mature in managed and natural habitats, we deployed traps in sweet and tart cherry orchards and nearby stands of the ancestral host tree, black cherry. Flies were removed from the traps and females were dissected to determine the presence of fully developed eggs. We found that capture of reproductively mature female flies occurred earlier in orchards that are not sprayed with insecticides than in sprayed orchards or in black cherry tree sites. In addition, the gap between the flights of immature and mature females in unmanaged sweet or tart cherry orchards was shorter than in managed orchards or black cherry tree sites. We also determined fruit color, size, and skin hardness to characterize the progression of fruit maturity. We found that fruit became mature earlier in sweet and tart cherry orchards than in black cherry tree sites. This study indicates that the timing of female reproductive maturity is plastic and varies among cherry fruit fly populations present in distinct habitats. Variation in the timing of reproductive maturity is related to the fruit maturity period of distinct host plant species and to orchard management.