Monitoring the outcome of restoration efforts is the only way to identify the status of a recovery and the most effective management strategies. In this paper, we discuss Chesapeake Bay and watershed recovery and factors influencing water quality trends. For over 30 years, the Chesapeake Bay Program Partnership’s long-term tidal and watershed water quality monitoring networks have measured physical, chemical and biological parameters throughout the bay and its surrounding watershed underpinning an adaptive management process to drive ecosystem recovery. There are many natural and anthropogenic factors operating and interacting to affect the watershed and bay water quality recovery responses to management actions. Across habitats and indicators, the bay and its watershed continue to express a diverse spatial and temporal fabric of multiscale conditions, stressors and trends that show a range of health conditions and impairments, as well as evidence of progress and degradation. Recurrent independent reviews of the monitoring program have driven a culture of continued adaptation of the monitoring networks to reflect ever evolving management information needs. The adherence to bay and watershed-wide consistent monitoring protocols provides monitoring data supporting analyses and development of scientific syntheses that underpin indicator and model development, regulatory assessments, targeting of management actions, evaluation of management effectiveness, and directing of priorities and policies.