Electrical distribution system operators (DSOs) are facing an increasing number of challenges, largely as a result of the growing integration of distributed energy resources (DERs), such as photovoltaic (PV) and wind power. Amid global climate change and other energy-related concerns, the transformation of electrical distribution systems (EDSs) will most likely go ahead by modernizing distribution grids so that more DERs can be accommodated. Therefore, new operational strategies that aim to increase the flexibility of EDSs must be thought of and developed. This action is indispensable so that EDSs can seamlessly accommodate large amounts of intermittent renewable power. One plausible strategy that is worth considering is operating distribution systems in a meshed topology. The aim of this work is, therefore, related to the prospects of gradually adopting such a strategy. The analysis includes the additional level of flexibility that can be provided by operating distribution grids in a meshed manner, and the utilization level of variable renewable power. The distribution operational problem is formulated as a mixed integer linear programming approach in a stochastic framework. Numerical results reveal the multi-faceted benefits of operating distribution grids in a meshed manner. Such an operation scheme adds considerable flexibility to the system and leads to a more efficient utilization of variable renewable energy source (RES)-based distributed generation.