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It is a good idea to wait until all of the leaves have fallen to begin raking. Raking too soon in the season may be a wasted effort. If there are more leaves on the trees, then more leaves will fall.  Watch the trees to determine when they are mostly or completely bare. Then, start your raking. If you have extra time on your hands, then you can also rake up the leaves as they begin to fall instead of waiting for all of them to fall. This will make your job easier when the last of the leaves fall, but it will also require raking a little at a time. In early fall, there might not be enough leaves on the ground to justify raking your whole lawn. However, if you have some early fall leaves that are bothering you, then you can mow them into your lawn. This will help to give your lawn extra nutrients and save you some time. Windy conditions will make raking more difficult. If possible, wait for a calm day to do your raking. However, if you have to rake on a windy day, then try to rake the leaves with the wind and not against it. For example, you could place your pile on the side of the yard that the wind is blowing towards. Then, rake all of your leaves in that direction. Check the leaves for dampness before you begin raking. If the leaves are wet, then they will be harder to rake. They will also weigh down the bags or other containers that you put them in, which will make it harder for you to move them. To make your job a little easier, wait until the leaves are dry to start raking them. Watch the weather and check the leaves before you get started.
Wait for all the leaves to fall. Mow early fall leaves into your lawn. Choose a calm day to rake. Ensure that the leaves are dry.