This dissertation explores the complex and multifaceted experience of freedom-seeking in Alexandria, Virginia, between 1820 and 1865. By examining various methods of resistance employed by enslaved individuals – including escape, violence, legal petitions, and wartime migrations – this study situates their actions within the broader historical, social, and legal contexts of antebellum and wartime Alexandria. As a city positioned at the intersection of the North and South, Alexandria played a unique role in the networks of slavery and resistance. It was a hub for the domestic slave trade and home to the infamous Franklin and Armfield firm, yet also a site of significant Black resistance. Using archival research, including runaway advertisements, court records, personal narratives, and newspaper reports, this dissertation reconstructs the lives of individuals who risked everything in pursuit of freedom. The following research is organized thematically, with each chapter focusing on a distinct method of resistance. Individual escapes, whether by land or sea, illustrate both the opportunities and obstacles present in Alexandria’s urban landscape. Violence as a form of self-liberation, including insurrections and personal acts of defiance, is examined within the context of both individual agency and systemic oppression. Legal challenges, such as petitions for manumission and freedom suits, reveal the shifting legal frameworks that sometimes allowed enslaved individuals to claim their freedom through judicial means. Group escapes and collective action highlight the strength of enslaved communities, as well as the networks of assistance available to fugitives. Finally, the Civil War years saw an influx of freedom-seekers into Alexandria, who transformed it into a freedom camp for formerly enslaved individuals, despite the complicated legality of slavery during the war. This study argues that freedom-seeking in Alexandria was not a series of isolated acts but rather an interconnected web of resistance shaped by geography, community, and evolving political landscapes. By viewing these varied forms of defiance as part of a broader struggle, this dissertation contributes to the historiography of American slavery and resistance, emphasizing the agency of enslaved individuals in their pursuit of liberation. The findings challenge conventional interpretations of escape and resistance, demonstrating the fluid and adaptive strategies employed by those who sought freedom in the shadow of enslavement.