Five sites in present-day New York have played important roles in archaeological narratives surrounding the development of settled village life in northeastern North America. Excavated in the mid-twentieth century, the Roundtop, Maxon-Derby, Sackett or Canandaigua, Bates, and Kelso sites include evidence related to the transition from semisedentary settlement-subsistence patterns during the twelfth through fourteenth centuries AD to those associated with fifteenth century and later settled Iroquoian villagers. Radiocarbon dates for each site were obtained early in the development of the method and again following the transition to AMS dating. Here, we present new or recently-published dates for these sites, combined with reliable existing dates in Bayesian models, including in some cases short tree-ring sequenced wiggle-matches on wood charcoal. Our results clarify the timing of each site’s occupation(s), revealing both continuity and discontinuity in the development of longhouse dwellings, sedentism, and the repeated re-use of some site locations over hundreds of years.