According to some embodiments, an improved tugger and rider cart assembly system is presented. The system comprising a tugger cart with a central space to receive a rider cart; the tugger cart having both front side and rear side pluralities of transport wheels approximately parallel to, but not touching, ground; a front side and a rear side loading wheel positioned closer to the ground than the transport wheels; a rider cart having a first wing and a second wing, both wings having a curved portion; and wherein the loading wheels and wing curved portions can be operatively connected to allow a user to move the rider cart onto the tugger cart thereby allowing the tugger cart to transport the rider cart.