Rapid and accurate crop aboveground biomass estimation is beneficial for high-throughput phenotyping and site-specific field management. This study explored the utility of high-definition digital images acquired by a low-flying unmanned aerial vehicle (UAV) and ground-based hyperspectral data for improved estimates of winter wheat biomass. To extract fine textures for characterizing the variations in winter wheat canopy structure during growing seasons, we proposed a multiscale texture extraction method (Multiscale_Gabor_GLCM) that took advantages of multiscale Gabor transformation and gray-level co-occurrency matrix (GLCM) analysis. Narrowband normalized difference vegetation indices (NDVIs) involving all possible two-band combinations and continuum removal of red-edge spectra (SpeCR) were also extracted for biomass estimation. Subsequently, non-parametric linear (i.e., partial least squares regression, PLSR) and nonlinear regression (i.e., least squares support vector machine, LSSVM) analyses were conducted using the extracted spectral features, multiscale textural features and combinations thereof. The visualization technique of LSSVM was utilized to select the multiscale textures that contributed most to the biomass estimation for the first time. Compared with the best-performing NDVI (1193, 1222 nm), the SpeCR yielded higher coefficient of determination (R2), lower root mean square error (RMSE), and lower mean absolute error (MAE) for winter wheat biomass estimation and significantly alleviated the saturation problem after biomass exceeded 800 g/m2. The predictive performance of the PLSR and LSSVM regression models based on SpeCR decreased with increasing bandwidths, especially at bandwidths larger than 11 nm. Both the PLSR and LSSVM regression models based on the multiscale textures produced higher accuracies than those based on the single-scale GLCM-based textures. According to the evaluation of variable importance, the texture metrics “Mean” from different scales were determined as the most influential to winter wheat biomass. Using just 10 multiscale textures largely improved predictive performance over using all textures and achieved an accuracy comparable with using SpeCR. The LSSVM regression model based on the combination of the selected multiscale textures, and SpeCR with a bandwidth of 9 nm produced the highest estimation accuracy with R2val = 0.87, RMSEval = 119.76 g/m2, and MAEval = 91.61 g/m2. However, the combination did not significantly improve the estimation accuracy, compared to the use of SpeCR or multiscale textures only. The accuracy of the biomass predicted by the LSSVM regression models was higher than the results of the PLSR models, which demonstrated LSSVM was a potential candidate to characterize winter wheat biomass during multiple growth stages. The study suggests that multiscale textures derived from high-definition UAV-based digital images are competitive with hyperspectral features in predicting winter wheat biomass.