During development, the fruit of some paprika (Capsicum annuum L.) cultivars shows a change in color from green to dark purple (e.g., ‘Mavras’) or lilac (e.g., ‘Tequila’). However, this purple coloration is rare among paprika cultivars and disappears in ripened fruit, which are red. Therefore, we investigated the mechanism causing this color change in the cultivars Mavras and Tequila to better understand how purple ripened fruit could be generated. High-performance liquid chromatography (HPLC) analyses of the anthocyanin contents of the fruit indicated that anthocyanin was undetectable in green fruit, accumulated in dark purple or lilac ones, and then decreased again in red ones in both cultivars. Furthermore, expressions of most of the analyzed anthocyanin biosynthesis–related genes and genes for their transcription factors increased in dark purple or lilac fruit and decreased in red ones, i.e., it was synchronized with the changes in anthocyanin contents. Furthermore, anthocyanin degradation activity as a result of peroxidases was detected at all stages but increased when the lilac or dark purple color started to fade. Thus, the development of purple coloration is caused by increased anthocyanin biosynthesis, whereas the fading of this coloration is a result of both a decrease in anthocyanin biosynthesis and an increase in anthocyanin degradation. At the ripening stage, the green pigment (chlorophyll) contents decreased, whereas the red pigment (carotenoid, particularly capsanthin) contents increased. However, these timings did not completely coincide with the timing of anthocyanin degradation, suggesting that the content of each pigment is individually regulated, and so purple, green, and red coloration could be freely expressed in mature paprika fruit.