Abstract: This dissertation is about places—what they are, why they matter, and how they contribute to making the world we share. I chart a triangular relationship between built materialities, histories, and social imaginaries to articulate how places come about, expand and constrain possibilities, and shape communities and projects. I focus on contested places to account for, and critique, settlers’ placemaking practices in colonized landscapes, with a particular attention to those processes on Mi’kma’ki, Wolastokuk, and Peskotomuhkatik, or what are commonly called the Maritime Provinces of Canada. The dissertation proceeds through an investigation of dilapidating settler structures in these places and the practices that sustain them. In Chapter One, I examine settlers’ nostalgic engagements with abandoned barns to problematize settler romanticizations of colonized landscapes. Chapter Two is about covered bridges and the difficulties of preserving places by holding onto their material components. In Chapter Three, I consider community negotiations around the construction of the Confederation Bridge to introduce my enactive account of placemaking and theorize placial change. This account explains what places are and why they matter; it also articulates the ways settler placemaking contributes to colonization. Chapters Four and Five are about the aboiteaux of the Chignecto Isthmus. Through an investigation of their history, I articulate an account of placial health and differentiate “places” from “nature”; through an investigation of the present threats they pose to the Isthmus in light of rising sea levels, I explain how histories constrain available possibilities for healthy placemaking in the present, and I chart some short-term avenues for enacting healthier places in an unjust world.