The objective of this paper is to present an overview of on-going work aimed at the development of a sensing system that can be applied toward the long term monitoring of pavement structures. The paper addresses the different challenges related to the successful development and implementation of the system for pavement application. The novel module consists of a miniaturized battery-less wireless sensor capable of detecting the long-term strain history of the pavement structure. It is based on the integration of piezoelectric transducers with an array of ultra-low power floating gate computational circuits. The paper is split into four sections. First, a summary of the development of the sensor electronics is provided. Then, a description of the development of a reliable packaging system that ensures structure integration of the sensor, reasonable survivability under construction conditions, and longevity in harsh environments, is presented. Also, a damage prediction algorithm to estimate the remaining life of the pavement from the sensor output data is discussed. Finally, the use of a probabilistic based interpolation technique for the estimation of full field strain distributions, using measured data from a limited number of implemented sensors, is investigated in the context of exploring the feasibility of large networks deployment.