Current interest in genealogy and family history has soared, but the research journey may be fraught. Original intentions may be inhibited and inevitably altered as the actual historical details are revealed and documented through recorded evidence. While liberties may be taken with memoir and even autobiography, critical family history requires scrutiny of the lived events uncovered—some of which may be in sharp contrast to family myths passed down through generations. I traveled to three states and conducted archival research in local libraries, court houses, historical county archives, and museums in my search for original sources of authentic information about the names listed on a family tree over centuries. This article reports on how and why research on the genealogy of two families joined by marriage shifted from a straightforward recording of chronological facts to the development of a novel. The case can be made that fiction provides an effective and engaging tool for the elaboration of interconnected lives through the addition of historical context, enriching personal details, and imagined dialogue. Key accuracies needed for a critical family history can be preserved but in a genre that enables characters and their stories to come to life.