Improved and more continuous condition assessment of bridges has been demanded by our society to better face challenges posed by aging civil infrastructure around the world. Indeed, the recent collapses of the Hintze Ribeiro Bridge that killed 59 people, in Portugal, and the I-35W Bridge over the Mississippi River that killed 13 people, in the United States, pointed out the need for the implementation of Bridge Management Systems (BMSs) with more reliable tools to avoid those events. Recent developments suggest that, in an effort to create more robust bridge management, in particular the improvement of the structural condition assessment, the concepts of Structural Health Monitoring (SHM) should be merged into the BMS, in a systematic way. Thus, in order to have a broad discussion on the past, present, and future of that topic, an International Seminar was held at the Catholic University of Portugal. This seminar intended to bring together bridge designers and owners, researchers, and students to discuss the current condition of the bridges in Portugal and to highlight shortcomings in current bridge inspection, condition assessment, and maintenance strategies. Therefore, this paper intends to summarize the highlights of the seminar, especially the main lessons from the past, the current needs and limitations, and some guidelines to improve the bridge management using SHM technology.