In fire‐prone ecosystems, knowledge of vegetation–fire–climate relationships and the history of fire suppression and Indigenous cultural burning can inform discussions of how to use fire as a management tool, particularly as climate continues to change rapidly. On Wiisaakodewan‐minis/Stockton Island in the Apostle Islands National Lakeshore of Wisconsin, USA, structural changes in a pine‐dominated natural area containing a globally rare barrens community occurred after the cessation of cultural burning by the Indigenous Ojibwe people and the imposition of fire‐suppression policies, leading to questions about the historical role of fire in this culturally and ecologically important area. To help understand better the ecological context needed to steward these pine forest and barrens communities, we developed palaeoecological records of vegetation, fire, and hydrological change using pollen, charcoal, and testate amoebae preserved in peat and sediment cores collected from bog and lagoon sediments within the pine‐dominated landscape. Results indicated that fire has been an integral part of Stockton Island ecology for at least 6000 years. Logging in the early 1900s led to persistent changes in island vegetation, and post‐logging fires of the 1920s and 1930s were anomalous in the context of the past millennium, likely reflecting more severe and/or extensive burning than in the past. Before that, the composition and structure of pine forest and barrens had changed little, perhaps due to regular low‐severity surface fires, which may have occurred with a frequency consistent with Indigenous oral histories (~4–8 years). Higher severity fire episodes, indicated by large charcoal peaks above background levels in the records, occurred predominantly during droughts, suggesting that more frequent or more intense droughts in the future may increase fire frequency and severity. The persistence of pine forest and barrens vegetation through past periods of climatic change indicates considerable ecological resistance and resilience. Future persistence in the face of climate changes outside this historical range of variability may depend in part on returning fire to these systems.