Permeable-pavement design methodologies can improve the hydrologic and therefore the environmental benefits of rural and urban roadway systems. By contrast, conventional impervious pavements perturb the hydrologic cycle, altering the relationship between the rainfall loading and runoff response. Impervious pavements create a hydraulically conductive interface for the transport of traffic-generated chemicals and particulate matter (PM), deleteriously impacting their proximate environments. Permeable-pavement systems are countermeasures to mitigate hydrologic, chemical, and PM impacts. However, permeable pavements are not always equally implementable due to costs, PM loadings, and design constraints. A potential solution to facilitate environmental benefits while meeting the traffic load capacity is the combination of two filtration systems placed at the pavement shoulders and/or pedestrian sidewalks: a bituminous-pavement open-graded friction course (BPFC) and an aggregate-filled infiltration trench. This solution is presented in this manuscript together with the methodological framework and the first results of the investigations into designing and validating such a combined system. The research was conducted at the laboratories of the Polytechnic University of Bari and the University of Florida, while an operational and full-scale physical model was constructed in Bari, Italy. The first results presented characterize the PM deposition on public roads based on granulometry (particle size distributions (PSDs) and particle number densities (PNDs)). Samples (n = 16) were collected and analyzed at eight different sites with different land uses, traffic, and pavements from different cities (Bari and Taranto, Italy). The PM analysis showed similar distributions (PSDs and PNDs), except for two samples. The gravimetric-based PSDs of the PM had granulometric distributions in the sand-size range. In contrast, the PNDs, modeled by a Power Law Model (PLM) (R2 ≥ 0.92), illustrated an exponentially increasing number of particles in the fine silt and clay-size range, representing less than 10% of the PSD mass. Moreover, the results indicate that PM sourced from permeable-pavement systems has differing impacts on the pavement service life.