The biggest threats to the longevity of a timber bridge are rot and decay. Wood protection by design, inspections, and monitoring of the bridge for elevated moisture content will ensure that the full service life of the structure can be achieved. Today’s sensors for moisture content measurements are limited in their functionality and range. This paper presents a sensor that can be both factory installed and retrofitted, which can measure the moisture content through the cross-section of the member in a timber bridge. The sensor has been mounted on Sundbron bridge during manufacturing and retrofitted on Gislaved bridge. The ensuing measurements helped to adjust a design flaw on Gislaved bridge. Monitoring of Sundbron showed that the bridge deck dried up after the bridge had been exposed to sleet and snow during the on-site assembly of the stress laminated bridge deck.