Maintenance of roadside ditches is important to avoid localized flooding and premature failure of pavements. Scheduling effective preventative maintenance requires a reasonably detailed mapping of the ditch profile to identify areas in need of excavation to remove long-term sediment accumulation. This study utilizes high-resolution, high-quality point clouds collected by mobile LiDAR mapping systems (MLMS) for mapping roadside ditches and performing hydrological analyses. The performance of alternative MLMS units, including an unmanned aerial vehicle, an unmanned ground vehicle, a portable backpack system along with its vehicle-mounted version, a medium-grade wheel-based system, and a high-grade wheel-based system, is evaluated. Point clouds from all the MLMS units are in agreement within the ±3 cm range for solid surfaces and ±7 cm range for vegetated areas along the vertical direction. The portable backpack system that could be carried by a surveyor or mounted on a vehicle is found to be the most cost-effective method for mapping roadside ditches, followed by the medium-grade wheel-based system. Furthermore, a framework for ditch line characterization is proposed and tested using datasets acquired by the medium-grade wheel-based and vehicle-mounted portable systems over a state highway. An existing ground-filtering approach—cloth simulation—is modified to handle variations in point density of mobile LiDAR data. Hydrological analyses, including flow direction and flow accumulation, are applied to extract the drainage network from the digital terrain model (DTM). Cross-sectional/longitudinal profiles of the ditch are automatically extracted from the LiDAR data and visualized in 3D point clouds and 2D images. The slope derived from the LiDAR data turned out to be very close to the highway cross slope design standards of 2% on driving lanes, 4% on shoulders, and a 6-by-1 slope for ditch lines.