The order Poales comprises a substantial portion of plant life (7% of all angiosperms and 33% of monocots) and includes taxa of enormous economic and ecological significance. Molecular and morphological studies over the past two decades, however, leave uncertain many relationships within Poales and among allied commelinid orders. Here we present the results of an initial project by the Monocot AToL (Angiosperm Tree of Life) team on phylogeny and evolution in Poales, using sequence data for 81 plastid genes (exceeding 101 aligned kb) from 83 species of angiosperms. We recovered highly concordant relationships using maximum likelihood (ML) and maximum parsimony (MP), with 98.2% mean ML bootstrap support across monocots. For the first time, ML resolves ties among Poales and other commelinid orders with moderate to strong support. Analyses provide strong support for Bromeliaceae being sister to the rest of Poales; Typhaceae, Rapateaceae, and cyperids (sedges, rushes, and their allies) emerge next along the phylogenetic spine. Graminids (grasses and their allies) and restiids (Restionaceae and its allies) are well supported as sister taxa. MP identifies a xyrid clade (Eriocaulaceae, Mayacaceae, Xyridaceae) sister to cyperids, but ML (with much stronger support) places them as a grade with respect to restiids graminids. The conflict in resolution between these analyses likely reflects long-branch attraction and highly elevated substitution rates in some Poales. All other familial relationships within the order are strongly supported by both MP and ML analyses. Character-state mapping implies that ancestral Poales lived in sunny, fire-prone, at least seasonally damp/wet, and possibly nutrient-poor sites, and were animal pollinated. Five subsequent shifts to wind pollination—in Typhaceae, cyperids, restiids, Ecdeiocoleaceae, and the vast PACCMAD-BEP clade of grasses—are significantly correlated with shifts to open habitats and small, inconspicuous, unisexual, and nectar-free flowers. Prime ecological movers driving the repeated evolution of wind pollination in Poales appear to include open habitats combined with the high local dominance of conspecific taxa, with the latter resulting from large-scale disturbances, combined with tall plant stature, vigorous vegetative spread, and positive ecological feedback. Reproductive assurance in the absence of reliable animal visitation probably favored wind pollination in annuals and short-statured perennials of Centrolepidaceae in ephemerally wet depressions and windswept alpine sites.