Accurate mapping of headwater streams and their flow status has important implications for understanding and managing water resources and land uses. However, accurate information is rare, especially in rugged, forested terrain. We developed a streamflow permanence classification model for forested lands in western Oregon using the latest light detection and ranging-derived hydrography published in the National Hydrography Dataset. Models were trained using 2,518 flow/no flow field observations collected in late summer 2019–2021 across headwaters of 129 sub-watersheds. The final model, the Western Oregon WeT DRy model, used Random Forest and 13 environmental covariates for classifying every 5-m stream sub-reach across 426 sub-watersheds. The most important covariates were annual precipitation and drainage area. Model output included probabilities of late summer surface flow presence and were subsequently categorized into three streamflow permanence classes—Wet, Dry, and Ambiguous. Ambiguous denoted model probabilities and associated prediction intervals that extended over the 50% classification threshold between wet and dry. Model accuracy was 0.83 for sub-watersheds that contained training data and decreased to 0.67 for sub-watersheds that did not have observations of late summer surface flow. The model identified where predictions extrapolated beyond the domain characterized by the training data. The combination of spatially continuous estimates of late summer streamflow status along with uncertainty and extrapolation estimates provide critical information for strategic project planning and designing additional field data collection.