The Pequot author William Apess is regarded as having almost miraculously transcended poverty, racism, and injustice to become an eloquent orator. Modern scholars have imagined the place of his birth as a primitive camp in the hills. Yet Colrain, in the early 1800s, was a bustling, religiously diverse, transcultural town where white (mostly Scots- Irish), Native American, and African American people routinely crossed paths, and where the Apess family routinely crossed color lines. Over time, Apess drew on his experiences among tribal, racial, and religious groups in multiple locales (Colchester, Colrain, Ledyard, Mashpee, Tyendinega, and elsewhere) to construct a compellingly romanticized (and colonized) version of indigenous identity. Onstage and in print, he was an iconic “poor Indian” and “son of the forest”; in person, he was a well-educated, cosmopolitan performer who loved the limelight and feared the wilderness. He evoked a precolonial ideal of a pristine Native life, while delivering trenchant critiques of white settler abuses; yet he advocated for religious conformity more than for indigenous survivance. Thus, to better contextualize Apess’ life and works, we need to critically and carefully consider nineteenth-century modes of identity formation, national affiliation, cultural performance, and racial tropes, including those articulated by Apess himself.