Phenological shifts across plant species is a powerful indicator to quantify the effects of climate change. Today, mobile applications with automated species identification open new possibilities for phenological monitoring across space and time. Here, we introduce an innovative spatio-temporal machine learning methodology that harnesses such crowd-sourced data to quantify phenological dynamics across taxa, space and time. Our algorithm links individual phenological responses across thousands of species and geographical locations, using a similarity measure. The analysis draws on nearly ten million plant observations collected through the AI-based plant identification app Flora Incognita in Germany from 2018 to 2021. Our method quantifies changes in synchronisation across the annual cycle. During the growing season, synchronised behaviour can be encoded by a few characteristic macrophenological patterns. Nonlinear spatio-temporal changes of these patterns can be efficiently quantified using a data compressibility measure. Outside the growing season, the phenological synchronisation diminishes introducing noise into the patterns. Despite biases and uncertainties associated with crowd-sourced data, for example due to human data collection behaviour, our study demonstrates the feasibility of deriving meaningful indicators for monitoring plant macrophenology from individual plant observations. As crowd-sourced databases continue to expand, our approach holds promise to study climate-induced phenological shifts and feedback loops.