Archaeological Investigations in the upper Roaring Creek Valley have revealed a complex Maya Landscape of settlements and ritual cave sites. This paper reports on data recorded at these settlements, which, also provides excellent evidence for local continuities and discontinuities in Classic Maya culture and the uneven changes and transformations of the Terminal Classic period. This is particularly true of sites such as Cahal Uitz Na and Chaac Mool Ha, and Pook's Hill. Several caves and rockshelters have also been investigated in the valley and they reflect a peak in ritual cave utilization between 800 and 900 AD. The Terminal Classic period brought with it great challenges to the traditional Classic period style of life for the Maya and many communities were unable to cope, which is evident by the large-scale decline and abandonment of many formerly successful city-states. Depopulation in this area was likely prompted by this broader set of social and political stresses and partly brought on by environmental degradation.