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When should I clean my gutters?
A good rule of thumb is twice a year: once in spring, and again in fall after most leaves are down. Set a yearly reminder so you don't have to remember.
Why spring and fall?
Delaware's environmental agency suggests clearing gutters about twice a year, in spring and early fall, and any time a blockage forms. NC State Extension says to inspect gutters yearly and after major weather events. In central North Carolina, fall color usually peaks around the last week of October through the first week of November (ABC11), and the leaves come down after that, so a later fall check catches more of them.
Also look after big storms: if water spills over the edge or you see plants growing up there, don't wait for the reminder.