At Barrow, Alaska, local Iñupiat whaling crews annually construct a network of seasonal trails through the shorefast ice during the traditional spring hunting season. These trails originate at locations along the coast and pass through diverse ice features, including ridged and rubbled ice, new and potentially flooded ice, and tidal cracks, before terminating at the shorefast ice edge where camps are established. The safety of this hunt relies on the careful observation of evolving ice characteristics from freeze-up onward and the understanding of how the interplay between ice dynamics, ice thermal evolution, and ocean and atmospheric processes leads to both stable and dangerous conditions. Partnering with Barrow whalers, a multi-year documentation of whaling trails, alongside a geophysical record of shorefast ice conditions, provides insight into how Iñupiat hunters monitor the development of the shorefast ice throughout winter and spring and how individual and community assessments of ice conditions and associated risks, traditions and knowledge, and personal preference determine trail placement. This contribution also discusses how the documentation of human use of the ice environment contributes to integrated observations of Arctic change and adaptation.