You just have to be alert to bypassing them when needed. Slightly fancier (but still traditional) versions have pails or cups with holes in the bottom that direct the water down the chain. How To Winterize Rain Barrels And Garden Hoses In Order To Keep Rain Barrels And Hoses In Good Condition For Next Rain Barrel Garden Hoses Rain Barrel System Click here to view all of our rain chain accessories. How do rain barrels work in the winter . A rain barrel is any type of container used to catch water flowing from a downspout. Rain barrels commonly have a large hole at their top onto which the downspout of the catchment system is connected. As with any roof drainage, if possible, direct it away from impervious surfaces like concrete and asphalt to slow it down, spread it out, and soak it in. For the most part, water won’t be running off your roof. Once drained, turn the barrel upside down, if possible, to empty it completely. When it rains, the rain barrel will be filled with ra...