Secondary metabolites, namely, phenolic and volatile organic compounds, contribute to the nutritional and organoleptic quality of the strawberry fruit. This study focuses on the changes in the content of phenolic compounds and volatile organic compounds during the ripening, from green to overripe fruit, of five strawberry cultivars (‘Asia’, ‘CIVN 766’, ‘Aprica’, ‘Clery’, and ‘Malwina’). Additionally, these changes are compared with the colour of the fruit and peroxidase and polyphenol oxidase activity. Our results show that the accumulation of secondary metabolites (phenolic and volatile organic compounds) significantly changed during the ripening process for all of the studied cultivars. As for phenolic compounds, flavanols and hydroxybenzoic acid derivatives comprised between 87 and 95% of the total phenolic compound content in unripe green fruit. In contrast, anthocyanins and hydroxycinnamic acid derivatives comprised between 64 and 77% of the total phenolic compound content in overripe fruit, except in the fruit of the cultivar ‘CIVN766’. When it comes to the aroma profile, the content of aldehydes decreased by 24–49% as the fruit ripened, and the accumulation of esters increased. Our study also shows that the ripening process differs among cultivars, and it is therefore necessary to define ripening indicators separately for each cultivar.