While much research has been done to utilise historic flood data, much more work is required to understand richly nuanced historic human relationships with water qualitatively. This article combines an in-depth oral history interview with a retired Cumbrian Land Drainage and Flood Risk Management engineer, whose career spanned from 1978 to 2011, with the documentary archives of the largely overlooked local Drainage Boards (DBs) and their successors after the Land Drainage Act (1930), Internal Drainage Boards (IDBs). These boards were established across Cumbria and the rest of England from the early nineteenth century to organise the collection of communal drainage rates charged by hectare of land to fund the installation and maintenance of flood prevention infrastructure. The records of these locally-specific, flexible and relatively small drainage boards demonstrate loudly and clearly the benefits of decentralised flood management, able to respond directly to the particularities of their own catchment's environment, residents, economy, infrastructure, topography and climatic challenges. It is vitally important to listen to the voices contained in the minute books of IDBs because they counterbalance historiographically-dominant narratives of top-down, large-scale infrastructural installations, inflexible centralisation of water governance and the powerlessness and gradual demise of many similarly small-scale, locally rooted and bottom-up organisations. The article argues that these local collectives, while far from being environmentalist, were nevertheless deeply in touch with the landscapes and waterscapes they managed and with intergenerational understanding of and respect for the watery environments within their boundaries. DBs and IDBs developed strong, deep and dynamic relationships with water as it coursed through the Cumbrian landscape. These boards also forged long-term relationships with central government and the Ministry of Agriculture. Those who served on Drainage Boards were regulators and stewards of the English landscape and their archival voices can tell us a great deal about how and why human relationships with water changed over the nineteenth and twentieth centuries.