Lately, and to my surprise, one of the most useful books in my repertoire has been AD&D's Oriental Adventures. There are Yearly and Monthly Events charts in there that are incredibly useful for coming up with an outline for any location the PCs will spend much time in. They require a good bit of interpretation, especially as they're intended for a more Eastern setting and mine is decidedly Western in tone. Still, here are the yearly event results for Arcte, the town my PCs are currently occupying. I'm only revealing the chart up to September as that's the in-game month.
I didn't roll a Yearly Event, as I had something in mind for that already.
1079March: Major Fire, Cold Weather Delays Planting
April: VIP Visit
May: No Event
July: Bandit Activity
September: Notorious Criminal
The Winter of 1077 was unusually cold, stretching on into April of 1078. Planting was delayed so the harvest will be terrible, probably depleting the food stores and leading to popular unrest. In addition, a major fire in the Library of Arcte destroys valuable texts. Note: the fire was Essential Flame.
A Kentrian Magistrate arrives in April to present gifts to the Goddess Ea. Votaries, perfumes, and attractive slaves.
May is calm, but as summer arrives the growing unrest leads to questionable arrests of foreign merchants and traders. Locals turn to banditry in the roads and woods free of the influence of the Blasted Plains.
The al-Mari and al-Hans tribes arrange a marriage of heirs. The al-Mari heir will be sheikh of both tribes when he reaches 40.
In September a thief locals call the Crimson Flame begins robbing wealthy traders, but evades capture.