To quantify the effects of climate change on fruit production in Germany, this study aimed at determining long-term trends in winter chill, as calculated with the Chilling Hours and Dynamic Models (Chill Portions). An idealized daily temperature curve was used to convert daily temperature records from 43 weather stations, taken throughout the twentieth and late nineteenth centuries, into an hourly dataset, which was then converted to units of winter chill. Besides exposing temporal trends in winter chill, the data could be spatially interpolated, yielding contiguous maps of typical winter chill in Germany around 2010, as well as chilling losses since 1950. Throughout Germany, winter chill varied between 1700 and 3000 Chilling Hours or 125 and 150 Chill Portions. The areas of highest winter chill were located in the northern parts of the country. For the whole of Germany, there were no significant temporal trends. The extent of interregional variation in winter chill depended on the chilling model used. While the Chilling Hours Model showed strong declines in winter chill for the areas around Dresden and Leipzig, as well as for the Lake Constance region, the Dynamic Model did not detect such dramatic changes. More than a decline in winter chill, increased heat during the winter months might become a challenge to German fruit growers. As already experienced during the extraordinarily warm winter of 2006/07, warm temperatures during the winter can cause fruit trees that fulfill their chilling requirements relatively early to bloom prematurely. This can then lead to elevated risk of frost damage and hamper the homogeneity of flowering.