Circadian rhythms are endogenous oscillations, widely found across biological species, that have the capability of entraining to the 24-h light-dark cycle. Circadian systems often consist of both central oscillators that receive direct light-dark input and peripheral oscillators that receive input from the central oscillators. In this paper, we address questions related to what governs the time to and pattern of entrainment of these hierarchical circadian systems after an abrupt switch in the light-dark phasing. For a network consisting of a single central oscillator coupled to a chain of N feed-forward peripheral oscillators, we introduce a systematic way to derive an N-dimensional entrainment map whose fixed points correspond to entrained solutions. Using the map, we explain that the direction of reentrainment can involve fairly complicated phase advancing and delaying behavior as well as reentrainment times that depend sensitively on the nature of the perturbation. We also study the dynamics of a hierarchical system in which the peripheral oscillators are mutually coupled. We study how reentrainment times vary as a function of the degree to which the oscillators are desynchronized at the time of the change in light-dark phasing. We show that desynchronizing the peripheral oscillators can, in some circumstances, speed up their ultimate reentrainment following perturbations.