Polyphenol rich and especially anthocyanin rich berries like bilberries (Vaccinium myrtillus L.) and derived products such as wine have enjoyed increasing popularity. During winemaking and aging, the phenolic profile undergoes distinct changes, a phenomenon that has been well investigated in grape wine but not in bilberry wine. The present study determined the influence of different fermentation strategies including various pre- and postfermentative heating and cooling concepts on the phenolic profile of bilberry wine. Besides significant differences in total anthocyanin and tannin concentrations, the different fermentation strategies resulted in distinguishable anthocyanin profiles. A very fast aging manifested by a rapid decrease in monomeric anthocyanins of up to 98% during a 12 week storage and a coincident formation of polymeric pigments and pyranoanthocyanins was observed. Several well-known processes associated with production and aging of wine were much more pronounced in bilberry wine compared to grape wine.