Analyses of a sediment core from Little Pond, located in the town of Bolton, Massachusetts, provide new insights into the history of environmental and ecological changes in southern New England during the late Holocene. Declines in organic content and peaks in the abundance of Isoetes spores indicate reduced water depth at 2900–2600, 2200–1800, and 1200–800 calibrated years before present (cal yr BP), generally consistent with the timing of dry conditions in records from elsewhere in the northeastern United States. The Little Pond pollen record features little change over the last 3000 yr, indicating that the surrounding vegetation was relatively insensitive to these periods of drought. The 1200–800 cal yr BP dry interval, however, coincides with increased abundance of Castanea pollen, suggesting that the expansion of Castanea in southern New England may have been influenced by late-Holocene climatic variability.