Despite their ubiquity and importance as freshwater habitat, small headwater streams are under monitored by existing stream gage networks. To address this gap, we describe a low-cost, non-contact, and low-effort method that enables organizations to monitor streamflow dynamics in small headwater streams. The method uses a camera to capture repeat images of the stream from a fixed position. A person then annotates pairs of images, in each case indicating which image has more apparent streamflow or indicating equal flow if no difference is discernible. A deep learning modelling framework called Streamflow Rank Estimation (SRE) is then trained on the annotated image pairs and applied to rank all images from highest to lowest apparent streamflow. From this result a relative hydrograph can be derived. We found that our modelled relative hydrograph dynamics matched the observed hydrograph dynamics well for 11 cameras at 8 streamflow sites in western Massachusetts. Higher performance was observed during the annotation period (median Kendall’s Tau rank correlation 0.75 with range 0.6–0.83) than after it (median Kendall’s Tau 0.59 with range 0.34 – 0.74). We found that annotation performance was generally consistent across the eleven camera sites and two individual annotators and was positively correlated with streamflow variability at a site. A scaling simulation determined that model performance improvements were limited after 1,000 annotation pairs. Our model’s estimates of relative flow, while not equivalent to absolute flow, may still be useful for many applications, such as ecological modelling and calculating event-based hydrological statistics (e.g., the number of out-of-bank floods). We anticipate this method will be a valuable tool to extend existing stream monitoring networks and provide new insights on dynamic headwater systems.