The long-term “Grain-to-Green Program” (GGP) on China’s Loess Plateau is a major global ecological engineering project which has significantly boosted vegetation renewal. Some studies have found that the rate of restoration is quite rapid during the implementation of ecological engineering, however, the influence of multi-scale climatic conditions on the performance of ecological engineering is unclear. In this study, multiple sources of remote sensing data were used to estimate the dynamics of vegetation structural and functional indicators, water-related local climatic factors, and atmospheric circulation factors. These datasets were also used to detect possible causes for vegetation restoration on the Loess Plateau over the past 20 years. The results show that widespread increases in rates of normalized difference vegetation indexes (NDVI), leaf area indexes (LAI), gross primary production (GPP), and aboveground biomass carbon (ABC) during 2000–2016 were significantly higher than before 2000. GPP was significantly correlated with rainfall and surface runoff on a monthly scale, and there were significant positive correlations between GPP and atmospheric circulation. Our results demonstrate that both vegetation structural and functional indicators rapidly increase, and ecological engineering greatly accelerated vegetation restoration after 2000. Local climatic conditions and atmospheric circulation patterns enhance vegetation growth and impact of ecological engineering.