Strain is one of the most frequently monitored parameters in civil structural health monitoring (SHM) applications, and strain-based approaches were among the first to be explored and applied in SHM. There are multiple reasons why strain plays such an important role in SHM: strain is directly related to stress and deflection, which reflect structural performance, safety, and serviceability. Strain field anomalies are frequently indicators of unusual structural behaviors (e.g., damage or deterioration). Hence, the earliest concepts of strain sensing were explored in the mid-XIX century, the first effective strain sensor appeared in 1919, and the first onsite applications followed in the 1920′s. Today, one hundred years after the first developments, two generations of strain sensors, based on electrical and fiber-optic principles, firmly reached market maturity and established themselves as reliable tools applied in strain-based SHM. Along with sensor developments, the application methods evolved: the first generation of discrete sensors featured a short gauge length and provided a basis for local material monitoring; the second generation greatly extended the applicability and effectiveness of strain-based SHM by providing long gauge and one-dimensional (1D) distributed sensing, thus enabling global structural and integrity monitoring. Current research focuses on a third generation of strain sensors for two-dimensional (2D) distributed and quasi-distributed sensing, based on new advanced technologies. On the occasion of strain sensing centenary, and as an homage to all researchers, practitioners, and educators who contributed to strain-based SHM, this paper presents an overview of the first one hundred years of strain sensing technological progress, with the objective to identify relevant transformative milestones and indicate possible future research directions.