With the transition to LED lighting technology, multispectral night-time sensors are needed to quantify the changing nightscapes, given the limitations of the panchromatic sensors. Our objective was to quantify the contribution of lighting sources as measured on the ground and examine their correspondence with night-time brightness and color as measured from space. We conducted ground-based measurements of night-time brightness using the multidirectional (top, rear, right, front, left) and multispectral LANcube v2, which was mounted on the roof of a car, over 458 km of roads in central Israel and in Brisbane, Australia. For spaceborne measurements, we used the SDGSAT-1 multispectral Glimmer sensor. We found that spaceborne measurements of apparent radiance were best explained when including all ground-based directional measurements, with greater explanatory power for highways (R2 = 0.725) than for urban roads (R2 = 0.556). Incoming light in the five directions varied between road classes and land use. In most cases, the variability in night-time brightness and color was greater for urban road sections than for highways. We conclude that due to the spectral mixture of lighting sources, at a medium spatial resolution, the impact of the transition to LED lighting may be more easily recognized from space over highways than in dense urban settings.