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2.
The holiday season or Thanksgiving, Christmas, New Years, and any other holidays that fall into that time frame. It's called that because people of all the holiday related stress contributes to increases of suicide.
Wow, three suicides on campus this month? That's why they call it the "Silly season"
by GHouck September 13, 2008
 
1.
A term for the period in the year where the media/press (particularly newspapers, tabloids) do not have enough articles to fill the paper/schedule, and so resort to unverifiable, trivial, irrelevant, stupid or hoax stories. Phrase used particularly in British satire.
When reading a newspaper: "'Buckingham Palace corridors are fitted with traffic lights to stop staff bumping into the Queen?' Must be silly season again."

http://news.bbc.co.uk/1/hi/magazine/4198990.stm

Examples of silly season stories:

"Senator John Kerry once rescued a hamster from the sea and massaged it back to life"
"Bebo tries to beam messages to Earth-like planet"
"A rabbit started a fire at Devizes cricket club in Wiltshire, causing more than £50,000 damage"
"A woman has bequeathed to her children a piece of fruit that has been in her family since 1921"
by Vanderdecken September 21, 2008
 
3.
any time when the silly things people do are frequently reported in the media
You know its silly season when the odd news section is chock full of new articles.
by The Return of Light Joker September 12, 2008
 
4.
A term, widely used in the NASCAR community to describe the rumor(s) on which driver may or may not be leaving his current team for another team and the end of his contract. This normally takes place around the 1/2 way point of the season.
"Hey, Scooter... did you hear that Dale Jarrett might be leaving RYR to drive for Michael Waltrip? And he'll drive a Toyota??"

"Yep... Silly Season is starting early this year."
by Thew May 11, 2006
 
5.
The political primary season in the United States, where the party rank-and-file select their candidates for elective office. So called because of the phony "issues" prospective candidates dredge up to get attention, which tend to have little to do with the real challenges facing the republic.

Thought to have originated in New Hampshire, the state with the first presidential primaries.
"The silly season is upon us!"
by Nicole S. March 15, 2006