Late May through early October is the window for exterior painting in Berkshire County. Paint needs the surface dry and the overnight temperature to stay above roughly 50°F while it cures, and outside that window neither holds reliably here. September is often the best month of all: low humidity, mild days, and cool nights that have not yet turned cold.
It is the nights that decide, not the days
A warm afternoon in April feels like painting weather. But paint keeps curing for hours after the last coat goes on, and if the temperature drops near freezing overnight, the film sets badly. It can look fine for a season and then fail early.
Most exterior products want the surface and the air above roughly 50°F through the cure. In this part of Massachusetts that reliably means late May to early October.
Humidity matters as much as heat
Wood that is damp underneath will push paint back off no matter how good the product is. After a stretch of rain, the siding needs days to dry, not hours.
That is why September is often the best month here. The humidity has dropped, the days are mild, and the nights have not turned cold yet.
Most of the job is not painting
On an exterior, the hours go into scraping, sanding, priming bare wood and caulking the joints. That is what decides whether the finish lasts five years or one.
If a quote is much cheaper than the others, the difference is almost always prep. Ask specifically how the bare wood gets primed and what happens at the joints.
One thing to settle before anyone starts
If your house was built before 1978, the old layers may contain lead, and there are rules about how that paint gets disturbed. This is worth raising yourself rather than waiting to be told.
Ask the contractor how they plan to handle it. The answer tells you a lot about how the rest of the job will go.