This study quantifies the capacity of near-surface remote sensing imagery (e.g. from unmanned aerial vehicles, smartphones, or fixed cameras) to accurately monitor crop phenology and physical disturbances to crop growth at field scales. Our analysis focuses on a pilot case study of winter wheat production in the states of Punjab and Haryana in northwest India, one of the world’s most important smallholder agricultural systems in terms of wheat production. Near-surface imagery was collected for 508 individual one-acre fields using inexpensive smartphone cameras operated throughout the growing season by farmers.