This thesis introduces and explores the complex interplay of a 'Heritage of Dictatorship' within a culture of protest. Promptly after the Chilean government announced a 30-peso Metro fare hike in Santiago in October 2019, a commonplace student-led fare evasion unexpectedly triggered an irruption of city-wide protests and riots. Many of Santiago's Metro stations were subsequently destroyed by fire and vandals. As the protests quickly moved from the city's Metro stations to Santiago's Plaza Italia, one of the most common catchphrases of the Estallido Social [social explosion] became 'no son 30 pesos, son 30 años' [it's not 30 pesos, it's 30 years]. This rallying slogan was in reference to the 30 years of failed transition from the extreme neoliberal policies of Pinochet's dictatorial regime. As the protests evolved from a focus on the rise in Metro fare, the social movement demanded a wholesale replacement of Pinochet's Constitution with a new democratic one. Throughout the Estallido Social, the dissenters contemplated their colonial and dictatorial traumatic past on the public streets of Santiago and on the virtual walls of social media. With protests lasting throughout Chile's severe COVID restrictions, they eventually culminated in a national plebiscite to determine the fate of Pinochet's Constitution. This study of the protestors' engagement with their dictatorial and colonial past is best framed through the lenses of several multidisciplinary fields. Memory Studies has richly contributed to the academic study of dictatorial legacies throughout Latin America and quickly became an essential component to this research project. In addition, Social Movement Studies and Museum Studies provided fundamental frameworks for several elements of this research project. That said, this research is primarily based on the interdisciplinary lens of Critical Heritage Studies. Critical Heritage Studies is, at its heart, an examination of how we interact with our past, and is therefore the ideal lens through which to explore the protestors' engagement with their intergenerational trauma. This research employs a qualitative approach to interpret how cultural heritage and memory guide people to navigate the relationship between past dictatorships and democracy during a national crisis. The intrinsic nature of participation and performativity to cultural heritage and protest is the cornerstone of this methodology. This study is built around a focused multi-sited ethnography, in conjunction with a digital ethnography, and semi-structured interviews. More specifically, this research concentrates on both those who participated in the virtual and physical spaces of protest through street art, performance, textile art [arpilleras], and music, along with those who engaged with the protests through their roles as museum and memory site professionals at both Londres 38 and the Museo del Estallido Social. Due to Chile's unique history, a Heritage of Protest has developed in parallel with the centuries of colonial, hierarchal, and dictatorial rule. Encompassed within that heritage, Chile has also cultivated a particular Heritage of Dictatorship, as a result of the personal and intergenerational trauma experienced by many Chileans throughout the long years of dictatorship and the following decades of transition. Chileans' fixation on their authoritarian past not only affects aspects of their daily lives but also permeates their social movements through a form of heritage activism. The Estallido Social established an environment that took Chileans' cultural heritage onto the streets, fostering a medium through which to observe and theorise both their Heritage of Protest and their Heritage of Dictatorship. In studying the aesthetics of protest and the movement's performative actions, the streetscape of protests gave voice to those who suffered from intergenerational trauma. In addition, formal settings such as museums and memory sites are an integral part of these heritage practices, and facilitate the decoding of a culture's coloniality and its Heritage of Dictatorship, and Heritage of Protest. Both Londres 38 and the Museo del Estallido Social's proximity to the protest's ground zero catalysed its engagement with the social movement through their own form of museum activism. This project offers a means to understand cultures of coloniality and authoritarianism years after they have returned to democracy, as they continue to reengage with their cultural loss through various means of powerful creation and performance.