In the Mexican state of Yucatán, the Industrial Revolution is intimately linked to the cultivation and commercialization of henequen (Agave fourcroydes). The second half of the nineteenth and the first decade of the twentieth century are most often referred to as the region’s Gilded Age. Some local families accrued immense wealth, while many peasants were essentially enslaved. The city of Mérida saw the construction of magnificent mansions, and the new port of Progreso was connected through thousands of kilometers of railroads. At the same time, the rural landscape experienced the foundation of countless new and the expansion of existing haciendas. In this article, we provide a comparison of the relational memory of local communities regarding three of these historical settlements: San Pedro Cholul, San Antonio Nohuayún, and San Antonio Sihó. We present the circumstances leading to the historical archaeology project at San Pedro and recount our efforts at involving its descendant community. In the face of the recent destruction of San Pedro’s core buildings, we end with a discussion about the potential fates of Yucatan’s henequen haciendas and a series of suggestions on how to safeguard related material remains, while allowing stakeholders to benefit from historic preservation.