Sigatona - The Land of Jo'Ril hexcrawl for Old School Essentials, Chapter 8

The Party:

• Arrn, level 3 magic user
• Wumpus, level 3 dwarf
• Waverly, level 3 ranger
• Andrew Price, level 3 cleric
• Gordon Binghampton, level 3 cleric
• Calvin Baily, level 2 thief

The PCs have reached the metropolis of Sigatona to level up and spend money. After a day of rest, head out to explore the city.

1. The city is divided into districts. It takes 10 minutes to travel from district to district. Asking around for district highlights will get you a list of shops in that district. You can spend an hour to find that shop. Shops generated in HEXROLL each have a proprietor. Many shops have a list of specific items that can be purchased at a discount. Many shop proprietors have QUESTS! After a while, the players started to get overwhelmed with quest options. I told them "you don't have to take the quest, there's just a reward here if you find their missing sword or kidnapped nephew in a dungeon."
2. Every hour spent in the city, I would roll 1d6 for a random encounter. On a 1, (or 1-2 depending on time of day and circumstances), I would roll up a random encounter from my old Cities sourcebook by Midkemia Press from 1980.
3. The cleric with a CON of 5 was approached by a charlatan selling tonics of vitality. He gave the cleric a free sample. The cleric tried it and re-rolled 3d6 for his CON for one day (he got 12). If he wanted more, he'd have to pay 10gp per vial. He also learned of a powerful alchemist who lived in a secret tower in the desert who made a permanent version.
4. The other cleric - who worships the literal "god of divine right of rulership, arbiter of succession, and patron of nobility" - made a huge donation (4000gp) to the temple in the hopes of strengthening the power of the politically weak archon (mayor) over the more powerful Merchant Guild (who are really in charge). This audacious display got the attention of the merchant guild who paid the party a visit to convey a message of "don't do that again, or else". Introduced a neat political villain. Fun!
5. Did some great role-playing back at the inn when one of the PCs was randomly asking about a cult they were investigating. As it happened, HEXROLL said the busboy at the inn was allied with the cult and one of the patrons of the inn was a member of the cult. So the busboy put the PC in contact with the cult member who then tried to recruit them! The PCs are going along with it for now hoping to get more information about this cult - what they're doing? where's their headquarters? who's their leader? Introduced a future villain - the leader of the cult who is also a former companion to the alchemist they are looking for.
6. No fighting tonight, just a lot of role-playing, exploring, and NPC interactions. Next week, they head north to a) deliver a box, b) search for evil cult hideout, c) search for hidden alchemist tower.

The gist is this - procedurally generated random results are coming together quite nicely with input and actions from the players to create an interesting, layers, and interconnected world via prompts, connections, and straight-up serendipity and happenstance.

I'm super impressed!