Historical New England Town Meetings have long had an important role in the collective imaginary as exemplary models of democratic participation. However, scholarly investigation has pointed to important limitations with respect to the democratic credentials of these assemblies. In this paper, we engage with recent theorising from deliberative democracy to provide an updated historical examination of the deliberative and democratic qualities of Town Meetings from the seventeenth to the nineteenth centuries. We show that Town Meetings provided a space to engage in meaningful deliberation in the context of settlers’ communities. Nonetheless, through analyses using the notions of deliberative culture and group style, we show that these communities featured deep anti-democratic norms that curtailed the democratic potential of these assemblies.