Caneberry crops (raspberry and blackberry) are globally commercialized specialty crops with a high fresh market value. Field management of canes and harvesting of fruits can be complicated by the presence of prickles (the botanically accurate term rather than spines or thorns) on the stems, petioles, and underside of the leaves. Both field management and fruit harvesting could be simplified by the development of cultivars with prickle-free canes. Scanning electron microscopy (SEM) was used to analyze and compare prickle development in different Rubus species. Comparisons were made between prickled vs. prickle-free red raspberry (Rubus idaeus L.), black raspberry (Rubus occidentalis L.), blackberry (Rubus hybrid), complex hybrid with purple fruit (R. occidentalis × R. idaeus), and the hairy and prickled wineberry (Rubus phoenicolasius Maxim). Samples from stems and leaves with petioles attached were used for imaging. There were distinct differences between prickled vs. prickle-free phenotypes in each species. The images of prickle development suggest that prickles either develop directly from glandular trichomes (in red raspberry and wineberry) or that the signal originates from glandular trichomes (in blackberry). Black raspberry prickle development was similar to that of blackberry, suggesting that prickles developed after a developmental signal from glandular trichomes rather than as a direct development from glandular trichomes. The prickle development in the purple hybrid was unique in the presence of one-sided lumps in the trichomes, which has not been seen in any other Rubus species to date; however, both prickled and prickle-free plants exhibited simple nonglandular trichomes. Unlike previous studies, an increase in the number of simple trichomes was not specific to prickle-free plants, but rather variability among the different genotypes was observed. This study adds to the basic understanding of prickle development in the genus Rubus as a first step in the development of prickle-free versions of important cultivars through gene-editing procedures for improving the ease of field management and harvesting.