We compared forest canopy heights and nitrogen concentrations in long-term research sites and in 2 × 2 km landscapes surrounding these sites along a substrate age gradient in the Hawaiian Islands. Both remote airborne and ground-based measurements were used to characterize processes that control landscape-level variation in canopy properties. We integrated a waveform light detection and ranging (LiDAR) system, a high-resolution imaging spectrometer, and a global positioning system/inertial measurement unit to provide highly resolved images of ground topography, canopy heights, and canopy nitrogen concentrations (1) within a circle 50 m in radius focused on a long-term study site in the center of each landscape; (2) for the entire 2 × 2 km landscape regardless of land cover; and (3) after stratification, for our target cover class, native-dominated vegetation on constructional geomorphic surfaces throughout each landscape. Remote measurements at all scales yielded the same overall patterns as did ground-based measurements in the long-term sites. The two younger landscapes supported taller trees than did older landscapes, while the two intermediate-aged landscapes had higher canopy nitrogen (N) concentrations than did either young or old landscapes. However, aircraft-based analyses detected substantial variability in canopy characteristics on the landscape level, even within the target cover class. Canopy heights were more heterogeneous on the older landscapes, with coefficients of variation increasing from 23–41% to 69–78% with increasing substrate age. This increasing heterogeneity was associated with a larger patch size of canopy turnover and with dominance of most secondary successional stands by the mat-forming fern Dicranopteris linearis in the older landscapes.