Harvest timing is challenging for hop growers as on-farm pressures such as weather, labor, or kilning capacity can constrain a grower’s picking window. This presentation explores how on-bine maturity influences Citra® hop quality by examining three consecutive harvest years of data where Citra® hops were harvested weekly at seven time points each season from the same three commercial hop yards in the Yakima Valley, WA. Hops were assessed for total essential oil content, hop acids concentration, hop storage index, volatile chemical profile, and dextrin-reducing enzymatic activity. Additionally, the aromatic properties of hop grinds were assessed to evaluate qualitative changes. Across all harvest years and fields, chemical analysis revealed that total oil content and α-acid concentration increased and plateaued mid-harvest season, while the hop storage index (HSI) remained low and stable. Dextrin-reducing enzyme activity decreased nearly linearly with harvest maturity. Most volatile aromatic compounds (e.g., geraniol, linalool, humulene, α-pinene) increased with harvest maturity, while humulene epoxides decreased. Other aromatic compounds not studied, such as sulfur-based volatiles, likely influenced observed sensory changes. Early-season Citra® hops exhibited green vegetable-like characteristics such as “grassy,” “green pepper,” and “melon,” whereas hops harvested mid-season exhibited the best combination of chemical, biochemical, and sensory traits sought by brewers, including “citrus,” “tropical,” and “resinous” notes. A distinct transition to late-harvested hops occurred rapidly after the optimal harvest window where resultant hops presented pungent “onion,” “garlic,” and “sweaty” aromas. This study supports the growing evidence that harvest timing is a crucial influencer of hop quality.