70's or 80's movie?

Help! Back in the early to mid 80’s I remember it being Christmas time and as tradition dictated, Annie was playing on tv. I was pretty young but I do recall having seen Annie at least a couple Christmases in a row. I remember another movie/show following Annie and recall having seen it before also but cannot figure out what it was. I only remember it was live action but very brightly colored. There was a train running off tracks on a checkerboard and there was a conductor driving with his arm out the window. The conductor was an old, gray haired, bearded man wearing the pin stripe denim overalls and conductor hat. This is all I remember. Does anyone know what this is from??