Drifting Cups on a Meandering Stream (Kyokusui-no-En) is a Poetry Party that had its origin In ancient China, and was introduced to Japan passing through Korea. The flow of the meandering stream was made clear using the flow visualization techniques, surface floating method, PTV and the numerical simulation. At the same time, the motions of floating cup, the floating speed, relating speed and the trajectory of the cup were also analysed by using an originally developed image processing technique. Based on these researches, the model channel was considered. To make this party interesting the channel must has the characteristic that the drifting cups take the random pass and stagnant at the unexpected place. This model channel is satisfied with these conditions and the fluid mechanics consideration is performed on the both points of the experimental visualization and numerical simulation.