"The Reaping' holiday (Eirmont/Tembirr 22) as Hallow'Hin
by Marc SaindonOk bad pun.
But the Five Shires has potential has a Halloween season setting. I could imagine the Halflings completing the harvests, slaughtering the livestock, and at the end of all this hard work, go on a celebration much like our own, with treats, cider, and merrymaking.
And then, thinking a bit more, maybe in this pre-television era, there would be Bards of the "College of Spooky Autumn" (yeah, better name needed) who would go around from town to town, entertaining audiences with cantrip-enhanced horror stories by the inn's fireplace. Sort of like the College of Whispers, but not actually malicious, with the focus of fear being more about cautionary tales and entertainment. The Spooky Bards would also have a lot of lore concerning monster habits and weaknesses (even if embellished by folklore), so off-season they are still a valuable resource, even if they're the odd emo halflings in the Shires.
(pic from: https://www.southcountyri.com/listing/makers-mark-hobbit-house-at-the-reserve/2223/)