Abstract: A trailer wind bypass system for inhibiting a trailer be tipped over by the wind. The trailer wind bypass system includes a trailer member comprising a box portion and a plurality of wheels. The box portion is designed for receiving items to be transported over the road. The wheels are rotatably coupled to the box portion to facilitate transportation of the box portion over the road. The trailer member is designed for being coupled to a tractor for pulling the trailer member over the road. The box portion of the trailer member comprises a plurality of vent assemblies to permit wind to pass through the box portion of the trailer member. At least one actuation assembly is operationally coupled to the vent assemblies. The actuation assembly is for selectively opening and closing the vent assemblies when the actuation assembly is actuated by a user.