Withering is a practice traditionally used in various regions to produce sweet or dry wines. During withering there is an increase in sugar content but also a modification in volatile compound profiles. Controlling metabolic changes through the dehydration process to obtain wines with desired characteristics is therefore a challenging opportunity. The effects of two different withering technologies, post-harvest or on-vine with blocked sap vessel flow, on the volatile profile of young and aged Corvina red wines was investigated. The results showed that modulation of wine aroma due to the withering process is associated with fermentative metabolites, such as esters, higher alcohols, and acids, as well as grape-related compounds such as C6 alcohols, terpenes and norisoprenoids. Significant differences were also found by comparing the two withering techniques. Post-harvest in a traditional “fruttaio” warehouse wines showed higher content of ethyl acetate, ethyl butanoate, β-citronellol and 3-oxo-α-ionol, whereas post-harvest withering on-vine increased β-damascenone in wines. The type of withering technique has an influence on the evolution of some aroma compounds during the aging of wine, among them linalool, (E)-1-(2,3,6-trimethylphenyl)buta-1,3-diene (TPB), n-hexyl acetate, ethyl acetate, ethyl 3-methylbutanoate, 3-oxo-α-ionol and β-damascenone.