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This study tests the hypothesis that the arrival of Europeans in Jamestown, Virginia, had a negative impact on the dental health of native populations in the Chesapeake Bay. Data were collected on three variables—dental caries, periapical lesions, and antemortem tooth loss—in a sample of 644 individuals from four prehistoric (n = 500) and two contact era ossuaries (n = 144) from the Potomac Creek site in Virginia (44ST2). Statistical analysis reveals a trend of declining dental health for the post-contact sample (chi-square; P<0.05). The temporally latest ossuary had the highest prevalence of all indicators. There is also a trend toward poor dental health for females relative to males. In particular, females have a higher prevalence of carious lesions and antemortem tooth loss than males. Sex differences in dental health probably correspond to sex-based differences in food production and preparation in this setting, since females likely ate more cariogenic foods. Multiple factors likely explain the general pattern of decline in dental health, including: (1) a change in diet involving greater consumption of carbohydrates, (2) increased exposure to infectious pathogens, (3) warfare and other forms of conflict, (4) strain on resources, and (5) increased population density.