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"Constant readers" of the Times[…] must have been often amused by watching the change which yearly comes over the great journal during the months of autumn. When Parliament is no longer sitting and the gay world is no longer gathered together in London, something very different is supposed to do for the remnant of the public from what is needed in the politer portions of the year. […] In the dead of autumn, when the second and third rate hands are on, we sink from nonsense written with a purpose to nonsense written because the writer must write either nonsense or nothing. We have, however, observed this year very strong symptoms of the Silly Season of 1861 setting in a month or two before its time.
1876 May 23, “Dunedin”, in Bruce Herald, volume IX, number 805, Tokomairiro, N.Z.: Joseph Mackay, →OCLC, archived from the original on 26 May 2017, page 6:
The amount of space at the disposal of newspapers, and the want of something to talk about and write about, produced that mild autumnal effect known as the silly season, which sets in when there is a lull in politics, and a dearth of news.
The Sasquatch has long since become the clown who is the life of the party, whom nobody ever takes seriously; the godsend of newspaper cartoonists in the silly season when politicians are on vacation.
2009 August 13, “News in the silly season: Flying rabbits, violent cows and drowning hedgehogs”, in Spiegel Online, archived from the original on 13 May 2016:
The Brits call it the "silly season." In Germany the media call it the Sommerloch, literally "the summer hole." What they are referring to is the fact that when politicians and businesspeople close up shop and go away for the major European summer holidays, the number of serious news stories tends to diminish—meaning desperate hacks need to find something else to fill the hole.
Yes, Virginia, there is a presidential election in 1984—and it has begun: A former Vice President goes ice fishing and poses with a puny perch dangling from his line. A 68-year-old Senator dons athletic shorts and runs a 60-yd. dash in a San Francisco track meet. […] Such hijinks can mean only one thing: the quadrennial silly season has started again.
Over time, the silly season in Catholic liturgy that peaked in the 1970s—"clown" masses (with the priest vested as Bozo or somesuch), free-for-all prayers that ignored the prescribed rite, dreadful pop music, inept "liturgical dance," a general lack of decorum—began to recede.
(idiomatic,sports) The early part of a competition’s offseason, where many roster and staff changes are made based on the outcome of the season just concluded.
(sports) The time of year when contract negotiations start, trades, and competitors change affiliations, frequently starting at mid-season or just before the start of free-agency, and extending to the start of the next season.