A pick mat connection system (10, 40) that enables components to be connectable horizontally, to adapt to varied work site sizes, or vertically, to adapt to varied weight demands. Employing anchor assemblies (10), comprising an anchor (12) and lock (14) structure, to permit multiple standardized mats (1) to be connected horizontally, both end to end, and side to side. Additionally, employing stack anchor assemblies (40), selectively vertically connectable by a lock or bolt assembly (50), which enables the layering of multiple mats (7), thereby increasing the effective mat thickness.