The cannabis market is volatile, and standardized postharvest practices remain underdeveloped. This study investigates how drying, curing, and storage affect the chemical and physical quality of hemp (Cannabis sativa L.) flower. Treatments reflected common industry practices: barn and oven drying (40 °C and 50 °C) for biomass, and controlled environment drying (15 °C, 60% RH) with two-week curing for trimmed, smokable flower. Effects on essential oil (EO) yield, terpene and cannabinoid composition, moisture, and color were evaluated in two high-CBD, β-myrcene-dominant cultivars grown outdoors. Analytical methods met standard validation criteria, ensuring reliable quantification of 18 terpenes (via GC-MS) and 14 cannabinoids (via HPLC). On average, barn drying took 4.9 days, controlled environment (CE) drying 6.5 days, and oven drying 21–30.5 hours. Drying methods that allowed slow drying on the stem (barn and CE) increased EO yields (41–157% above fresh), while oven drying at 50 °C caused a 51% reduction. Monoterpenes were especially sensitive to postharvest handling, showing significant losses during curing and storage, while sesquiterpenes were more stable. Total cannabinoid levels remained stable throughout postharvest handling; however, significant decarboxylation of acidic cannabinoids occurred during storage (6.3–81.8%), with THCA showing the highest rates of conversion. Cultivar differences were observed: ‘Von’ showed greater increases in EO yield and better postharvest stability but had lower cannabinoid levels, while ‘Southern Sunset’ had higher cannabinoid concentrations but greater terpene losses during handling. Overall, results indicate clear trends that terpenes are more affected by drying method, cannabinoids are more influenced by storage, and the magnitude of these effects is dependent on cultivar. This work supports the refinement and optimization of traditional, industry-relevant drying methods through applied research.