Political and military decisions, cultural and artistic contributions: such topics are one way to assess the case of Hellenistic Messenia. Another way, however, is to take a closer look at life within the region, at the types of communities in which people lived, at the settlement and population of the land. Even in the years following liberation we are told relatively little of such matters by ancient authors, making archaeology our best source of information. Both excavation and archaeological survey can make a substantial contribution to our understanding of the region at this time. Long-term excavation has been carried out at the site of Messene, as well as at other locations, while two major survey projects have targeted Messenia: the University of Minnesota Messenia Expedition (UMME) in the 1960s and the Pylos Regional Archaeological Project (PRAP) in the 1990s. The latter project, which was both intensive and systematic in its methodology, has especially shed light on changing settlement and land use patterns in its study region, centered around the Bronze Age Palace of Nestor in the southwestern part of Messenia. For our purposes here, we can examine two levels of settlement -- city and countryside -- drawing on this range of archaeological information.