Abstract Background and Aims: Research on concentration changes of volatile compounds during grape physiological development has focused on the period from veraison to harvest. This study compared the developmental changes in the major volatile compounds released after the crushing of Riesling and Cabernet Sauvignon grapes sampled from fruitset to harvest during the 2007–2008 season. Methods and Results: Volatile compounds were extracted from the headspace of crushed Riesling and Cabernet Sauvignon grapes sampled throughout berry development using solid-phase microextraction and analysed by gas chromatography–mass spectrometry. A multivariate statistical approach coupled with analysis of variance was applied to compare the developmental changes in volatile compounds for the two cultivars. In both cultivars, E-2-hexenal was the most abundant volatile compound, and it showed a significant increase in concentration after veraison. Benzene derivatives discriminated ripe Cabernet Sauvignon grapes, whereas monoterpenes and sesquiterpenes discriminated both cultivars pre-veraison with a broader range of terpenes observed in the Cabernet Sauvignon samples compared with the Riesling samples. At veraison, terpene production in both varieties was low, but Riesling grapes produced some terpenes (geraniol and α-muurolene) post-veraison. Generally, esters and aldehydes were the major class of compounds from Riesling grapes, while Cabernet Sauvignon showed a greater tendency to form alcohols. Conclusions: Both Riesling and Cabernet Sauvignon grapes had a more complex volatile compound composition pre-veraison than post-veraison. This study suggests that some compounds that contribute to grape aroma may be produced pre-veraison, and not simply accumulate after veraison. Significance of the Study: Understanding the timing of volatile compound production and cultivar differences will guide viticulture researchers and growers in the optimisation of vineyard strategies to enhance grape aroma attributes that may, in turn, contribute to wine aroma.