At Tedesco CC here North of Boston...we aerify (big holes) the first Mon-Wed. in May, and the third Mon-Wed. in August.
The first one has always been standard, but the second one has moved around. Our biggest Member-Guest is the first weekend in August each year, so it has happened directly after that some years. We have tried doing it in late October before...but in bad winter years the holes were still visible in April, which is not what we want.
It's never great to have your course aerated when the weather is good and you want to play, but I think it's best when growing conditions are still good, thus providing quick recovery. Usually both May (especially) and August aeration recovers well by 10 days, and back to perfect by 15.