Near-infrared (NIR) spectroscopy and NIR hyperspectral imaging (NIR-HSI) were compared for the rapid estimation of physical and mechanical properties of No. 2 visual grade 2 × 4 (38.1 mm by 88.9 mm) Douglas-fir structural lumber. In total, 390 lumber samples were acquired from four mills in North America and destructively tested through bending. From each piece of lumber, a 25-mm length block was cut to collect diffuse reflectance NIR spectra and hyperspectral images. Calibrations for the specific gravity (SG) of both the lumber (SGlumber) and 25-mm block (SGblock) and the lumber modulus of elasticity (MOE) and modulus of rupture (MOR) were created using partial least squares (PLS) regression and their performance checked with a prediction set. The strongest calibrations were based on NIR spectra; however, the NIR-HSI data provided stronger predictions for all properties. In terms of fit statistics, SGblock gave the best results, followed by SGlumber, MOE, and MOR. The NIR-HSI SGlumber, MOE, and MOR calibrations were used to predict these properties for each pixel across the transverse surface of the scanned samples, allowing SG, MOE, and MOR variation within and among rings to be observed.