The volatilomes of fresh and dried fruiting bodies of Calocybe gambosa were analyzed and compared in this study for the first time. Aroma compounds were extracted by means of liquid/liquid extraction, purified by solvent assisted flavor evaporation (SAFE), and identified by gas chromatography-mass spectrometry and olfactometry. An aroma extract dilution analysis (AEDA) was performed to identify the key flavor compounds, and the main volatiles were quantified by GC flame ionization detection. The key odor compound of fresh fruiting bodies of C. gambosa was (E)-non-2-enal, which, together with (E)-non-2-en-1-ol, was responsible for the characteristic flour-and cucumber-like odor. The aroma profile of commercially available dried fruiting bodies of C. gambosa showed a different pattern. In the dried fruiting bodies, odor compounds like 3-methylbutanoic acid were dominating, and (E)-non-2-enal was not detectable. Thus, the aroma quality of commercially available dried fruiting bodies of C. gambosa differs significantly from that of freshly collected specimens.