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The time for power washing gutters and how often you need to do the job depends on where you live and what type of trees and vegetation you have around your house.
As an example, if there are pine trees nearby you probably already know how the needles tend to get stuck inside the spout. A pressure washer will be your best friend to dislodge them. Keep an eye on the weather when you are planning to use pressure washing equipment.
Beyond the obvious discomfort of working with water outdoors in the cold, if temperatures are near freezing you could end up covering your entire house in ice! Therefore, in most areas the best time of the year to pressure wash your gutters is either spring, late summer or early fall.