Scholars have developed rich theories explaining how entrepreneurship spurs changes to the central and distinctive features, or identities, of geographic communities. However, less attention has been paid to the means by which entrepreneurship variably affects these identities, or why members of some communities perceive widespread changes following entrepreneurial action while others remain relatively unchanged. Through a multiple case study, which included two communities in Massachusetts that played host to entrepreneurs seeking to found legal cannabis dispensaries, I develop a theory of community identity work, defined as the process through which a community’s central and distinctive features are maintained or altered following exogenous shocks. Qualitative analyses of various data sources, including interviews, community meetings, observations and archival materials revealed how communities with identities rooted in history are more resistant to change than those with more tenuous ties, and that these differences will affect entrepreneurs’ strategies, regional complementing and, ultimately, the degree to which new ventures become central to how members understand their communities.