This volume contains the proceedings of the workshop Crossing the Walls in Enumerative Geometry, held in May 2018 at Snowbird, Utah. It features a collection of both expository and research articles about mirror symmetry, quantized singularity theory (FJRW theory), and the gauged linear sigma model. Most of the expository works are based on introductory lecture series given at the workshop and provide an approachable introduction for graduate students to some fundamental topics in mirror symmetry and singularity theory, including quasimaps, localization, the gauged linear sigma model...