Fresh blueberries are very susceptible to mechanical damage, which limits postharvest life and firmness. Softening and susceptibility of cultivars “Duke” and “Brigitta” to developing internal browning (IB) after mechanical impact and subsequent storage was evaluated during a 2-year study (2011/2012, 2012/2013). On each season fruit were carefully hand-picked, segregated into soft (<1.60 N), medium (1.61–1.80 N), and firm (1.81–2.00 N) categories, and then either were dropped (32 cm) onto a hard plastic surface or remained non-dropped. All fruit were kept under refrigerated storage (0°C and 85–88% relative humidity) to assess firmness loss and IB after 7, 14, 21, 28, and 35 days. In general, regardless of cultivar or season, high variability in fruit firmness was observed within each commercial harvest, and significant differences in IB and softening rates were found. “Duke” exhibited high softening rates, as well as high and significant r2 between firmness and IB, but little differences for dropped vs. non-dropped fruit. “Brigitta,” having lesser firmness rates, exhibited almost no relationships between firmness and IB (especially for non-dropped fruit), but marked differences between dropping treatments. Firmness loss and IB development were related to firmness at harvest, soft and firm fruit being the most and least damaged, respectively. Soft fruit were characterized by greater IB development during storage along with high soluble solids/acid ratio, which could be used together with firmness to estimate harvest date and storage potential of fruit. Results of this work suggest that the differences in fruit quality traits at harvest could be related to the time that fruit stay on the plant after turning blue, soft fruit being more advanced in maturity. Finally, the observed differences between segregated categories reinforce the importance of analyzing fruit condition for each sorted group separately.