The Nipmuc have a long, deep, and rich history of working with local medicinal plants, which are still actively used to treat symptoms of chronic conditions such as poor circulation, high blood pressure, and blood sugar imbalances. European encroachment into Nipmuc land beginning in the 16th century disrupted not only the ecosystems of Central Massachusetts, but also the community and health foundations the tribe depends on. Today, these medicinal plant beings can still be found along trails on the tribe’s recently reclaimed lands, part of a broader land-back initiative led by the Hassanamisco Nipmuc Band that seeks to weave Traditional Ecological Knowledge with western science. This analysis aims to deepen community understanding of how reclaimed ecosystems may be shifting away from optimal conditions for key native medicinal plants, specifically Vaccinium spp., Rubus spp., Vitis spp., and Comptonia peregrina, and to inform management strategies that support their continued presence. Five trail segments were surveyed using 100-meter transects, with data collected on medicinal plant presence, soil moisture, soil pH, opportunistic species, leaf litter depth, canopy cover, trail incline, and dominant vegetation. Through this work, species-specific plant assemblages were built, revealing patterns in where, how, and with whom these culturally significant plants tend to gather. These findings invite a deeper reflection on how we humans care for medicinal species. Rather than approaching them solely for what can be taken, this research encourages us to join in these gatherings, to preserve the health of species that continue to be integral to our own survival.