Urban stream restoration is growing globally, but there is much to learn from successes, failures, and evaluating tradeoffs in restoration practices. Significant time and resources have been invested towards restoring the structure and function of urban ecosystems and understanding and slowing the drivers of degradation. However, the rapid pace of urbanization and its effects on urban waters present an ever-growing challenge to environmental managers and restoration practitioners when identifying and prioritizing effective strategies for restoration and monitoring outcomes. Here, we synthesize major findings and papers originating from the 5th Symposium on Urbanization and Stream Ecology (SUSE5) and propose a new concept for monitoring restoration based on lessons learned. Efforts from SUSE5 showed that urban disturbances and restoration activities have strong localized impacts that can be challenging to detect and disentangle across broader watershed scales and longitudinal flowpaths. Most urban stream restoration projects are monitored at only one or a few locations that do not capture significant variability across stream reaches and longer flowpaths. Based on knowledge from SUSE5, we present a new concept called ‘restoration milestones.’ The restoration milestones concept proposes that the scale of stream monitoring over space and time can influence whether a stream restoration project is considered a success or failure. Therefore, answers to questions regarding restoration effectiveness and durability can be affected by spatial and temporal monitoring scales. Setting realistic restoration milestones involves establishing monitoring strategies that account for spatial and temporal variability. Tracking restoration performance through time across stream reaches along longitudinal flowpaths could aid in more accurately assessing project performance. We explore applications for evaluating restoration milestones along longitudinal stream flowpaths including: (1) identifying target areas of improvement along drainage networks, (2) accurately accounting for tradeoffs in habitat, protection of infrastructure, and water quality along flowpaths, and (3) detecting how far downstream the effects of stream restoration and stormwater management can be propagated. Monitoring across different spatial and temporal scales is an overlooked but critical factor in determining restoration success. Additionally, the scale of the restoration project itself can determine the type and magnitude of improvements. Expectations for what a restoration project can accomplish in terms of water quality improvements should be calibrated to the project’s spatial scale and evolution over time. Longitudinal studies of stream restoration help identify successes and failures along flowpaths.