Accurate determination of phenological information of crops is essential for field management and decision-making. Remote sensing time-series data are widely used for extracting phenological phases. Existing methods mainly extract phenological phases directly from individual remote sensing time-series, which are easily affected by clouds, noise, and mixed pixels. This paper proposes a novel method of phenological phase extraction based on the time-weighted dynamic time warping (TWDTW) algorithm using MODIS Normalized Difference Vegetation Index (NDVI) 5-day time-series data with a spatial resolution of 500 m. Firstly, based on the phenological differences between winter wheat and other land cover types, winter wheat distribution is extracted using the TWDTW classification method, and the results show that the overall classification accuracy and Kappa coefficient reach 94.74% and 0.90, respectively. Then, we extract the pure winter-wheat pixels using a method based on the coefficient of variation, and use these pixels to generate the average phenological curve. Next, the difference between each winter-wheat phenological curve and the average winter-wheat phenological curve is quantitatively calculated using the TWDTW algorithm. Finally, the key phenological phases of winter wheat in the study area, namely, the green-up date (GUD), heading date (HD), and maturity date (MD), are determined. The results show that the phenological phase extraction using the TWDTW algorithm has high accuracy. By verification using phenological station data from the Meteorological Data Sharing Service System of China, the root mean square errors (RMSEs) of the GUD, HD, and MD are found to be 9.76, 5.72, and 6.98 days, respectively. Additionally, the method proposed in this article is shown to have a better extraction performance compared with several other methods. Furthermore, it is shown that, in Hebei Province, the GUD, HD, and MD are mainly affected by latitude and accumulated temperature. As the latitude increases from south to north, the GUD, HD, and MD are delayed, and for each 1° increment in latitude, the GUD, HD, and MD are delayed by 4.84, 5.79, and 6.61 days, respectively. The higher the accumulated temperature, the earlier the phenological phases occur. However, latitude and accumulated temperature have little effect on the length of the phenological phases. Additionally, the lengths of time between GUD and HD, HD and MD, and GUD and MD are stable at 46, 41, and 87 days, respectively. Overall, the proposed TWDTW method can accurately determine the key phenological phases of winter wheat at a regional scale using remote sensing time-series data.