A large network of coastal trails on Hawai'i Island was recently designated as a National Historic Trail, but our understanding of the trail has been limited to historical documentation supported by scant archaeological data. The current study is based upon an archaeological survey of a 2-mile section of the trail in Kona where it crosses through a dozen ahupua'a (traditional Hawaiian land divisions), and considers the significance of the coastal trail in relation to Hawaiian land use and exchange. Findings suggest that a trail paved with waterworn stones followed the same straight route as the current trail, which has been affected by numerous historical era modifications. Along with similar known examples in Kona, this finding calls into question a common assumption that all precontact and early historical Hawaiian coastal trails meandered along the contours of the coast. In addition to supporting chiefly endeavors such as the collection of tribute during the annual Makahiki festival, it is suggested that the straight trail may have supported regular exchange of domestic commodities across ahupua'a boundaries in the prehistoric or premissionary eras, and broadens our anthropological perceptions of interdistrict exchange in relation to ahupua'a economics.