The use of very long spatial datasets from satellites has opened up numerous opportunities, including the monitoring of vegetation phenology over the course of time. Considering the importance of grassland systems and the influence of climate change on their phenology, the specific objectives of this study are: (a) to identify a methodology for a reliable estimation of grassland phenological dates from a satellite vegetation index (i.e., kernel normalized difference vegetation index, kNDVI) and (b) to quantify the changes that have occurred over the period 2001–2021 in a representative dataset of European grasslands and assess the extent of climate change impacts. In order to identify the best methodological approach for estimating the start (SOS), peak (POS) and end (EOS) of the growing season from the satellite, we compared dates extracted from the MODIS-kNDVI annual trajectories with different combinations of fitting models (FMs) and extraction methods (EM), with those extracted from the gross primary productivity (GPP) measured from eddy covariance flux towers in specific grasslands. SOS and POS were effectively identified with various FM×EM approaches, whereas satellite-EOS did not obtain sufficiently reliable estimates and was excluded from the trend analysis. The methodological indications (i.e., FM×EM selection) were then used to calculate the SOS and POS for 31 grassland sites in Europe from MODIS-kNDVI during the period 2001–2021. SOS tended towards an anticipation at the majority of sites (83.9%), with an average advance at significant sites of 0.76 days year−1. For POS, the trend was also towards advancement, although the results are less homogeneous (67.7% of sites with advancement), and with a less marked advance at significant sites (0.56 days year−1). From the analyses carried out, the SOS and POS of several sites were influenced by the winter and spring temperatures, which recorded rises during the period 2001–2021. Contrasting results were recorded for the SOS-POS duration, which did not show a clear trend towards lengthening or shortening. Considering latitude and altitude, the results highlighted that the greatest changes in terms of SOS and POS anticipation were recorded for sites at higher latitudes and lower altitudes.