Existing hillslope sediment transport models developed for low-relief, soil-mantled landscapes are poorly suited to explain the coupling between steep rocky hillslopes and headwater channels. Here we address this knowledge gap using a series of field and numerical experiments to inform a particle-based model of sediment transport by dry ravel—a mechanism of granular transport characteristic of steep hillslopes. We find that particle travel distance increases as a function of the ratio of particle diameter to fine-scale (<1 m) topographic roughness, in agreement with prior laboratory and field experiments. Contrary to models that assume a fixed critical slope, the particle-based model predicts a broad transition as hillslopes steepen from grain-scale to hillslope-scale mean particle travel distances due to the trapping of sediment on slopes more than threefold steeper than the average friction slope. This transition is further broadened by higher macroscale (>1 m) topographic variability associated with rocky landscapes. Applying a 2-D dry-ravel-routing model to lidar-derived surface topography, we show how spatial patterns of local and nonlocal transport control connectivity between hillslopes and steep headwater channels that generate debris flows through failure of ravel-filled channels following wildfire. Our results corroborate field observations of a patchy transition from soil-mantled to bedrock landscapes and suggest that there is a dynamic interplay between sediment storage, roughness, grain sorting, and transport even on hillslopes that well exceed the angle of repose.