Time it around the first hard frost
The best fall cleanup window is after most leaves have dropped but before the ground freezes. Doing it too early means round two a few weeks later; too late and matted, wet leaves are much harder to clear and can already be smothering the grass underneath.
Village lots: focus on beds and walkways
Smaller in-town properties usually need less large-scale leaf clearing and more attention to tidying beds, cutting back perennials, and clearing walkways and storm drains so water has somewhere to go once winter rain and snowmelt start.
Larger properties: manage volume in passes
Bigger lots out toward the vineyard country generate a lot more leaf and debris volume. Rather than waiting for one massive cleanup, doing two lighter passes, one in mid-fall and one after the last leaves drop, is usually more manageable and better for the lawn underneath.
Cut perennials back, but not too far
Most perennials benefit from being cut back after frost, but leaving a few inches of stem rather than cutting to the ground gives some winter protection to the crown of the plant.
Check gutters while you're out there
A fall cleanup is a good moment to glance at gutters and downspouts too. Clogged gutters overflow right onto beds and walkways below, undoing a lot of the cleanup work underneath them.
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