Fall is not a maintenance season in Maine so much as a deadline. Anything involving drying time, adhesion or standing water gets harder once nights stay below freezing.
The list below is ordered by how much it costs you to skip it.
Drainage comes first
Gutters full of oak leaves and white pine needles cannot move meltwater in January, and water that cannot leave the roof finds another way down.
Check that downspouts discharge away from the foundation while you are at it.
Deal with moss before it goes dormant under snow
Moss holds moisture against shingles and lifts their edges as it thickens. A wet Maine fall is prime growing weather for it.
Moss should be removed gently. Pressure washing strips granules and can do more damage than the moss did.
Schedule warm-weather work now
Treatments, sealing and most roof cleaning need dry surfaces and reasonable temperatures. In practice that means the work happens before the weather closes in.
If you are considering rejuvenation, the assessment is the part that needs to happen this season — the decision can follow.
Trim what overhangs the roof
Branches that touch or nearly touch the roof drop debris directly onto it, keep sections permanently shaded and scuff granules in wind.
Clearance also reduces the load risk during the first heavy wet snow.
Why this is different here
In heavily wooded towns like Standish and Buxton, needle drop alone can fill a gutter run twice between September and November. One clearing in early October is often not enough; plan on checking again after the leaves finish.