Gutter cleaning is necessary as often as required to keep the gutters free of debris so that water can drain off the roof and run away from the from structure. When gutters become clogged with debris, the water can pool in the trough and run back up under the edge of the roof, so gutter cleaning is important. If you have a lot of trees on your property, gutter cleaning may be required twice a year. Leaves, twigs, dirt from the roof, and other debris collects in the gutters, even if you live in the middle of a field. Gutters should be cleaned late in the fall, after leaves have dropped from the trees. Monitor the situation and check the gutters in the spring to see if another cleaning is necessary before the seasonal rains begin.