This paper investigates the Collaborative Routing Orchestration for Organic Food Distribution Problem (CRO-FDP), a two-echelon collaborative distribution network setting inspired by a regional organic food network in Québec, Canada. The CRO-FDP integrates hub selection, vehicle routing, and synchronization decisions under tight time constraints to coordinate multiple producers and food banks sharing logistics resources. We develop a mixed-integer model and a time-expanded reformulation that jointly capture routing and timing decisions across a discretized planning horizon. A dedicated Relax–Solve–and–Fix matheuristic leverages this reformulation to efficiently solve realistic instances beyond the reach of standard formulations. Computational experiments demonstrate that the time-expanded model consistently yields feasible and near-optimal solutions for medium and large instances, outperforming the compact formulation. Results reveal significant efficiency and sustainability gains: collaborative pooling and hub usage reduce total travel distance by up to 1,000 km—an average decrease of 28%—and lower fleet requirements while maintaining service quality. These findings emphasize the strategic value of orchestration and hub-based collaboration for enhancing the environmental and economic performance of regional food distribution systems.