Standard but can still be forgettable by people like me lol

A local holiday or festival is always fun. It makes the world feel a bit more alive and gives NPCs something to talk about, it provides a handy deadline for certain quests, and it gives you an excuse to have merchants, performers, and other outsiders that might not usually be in a small town.

I usually just click the like button on these sort of posts, but several people had such good ideas I wanted to say thanks!

Glad you enjoyed the thread lol 

Honestly I would have thought a Magic Item Shop doesn’t fit in 5e.  DMG suggests Magic Items are too rare and valuable to just share in a shop or at auction.  Still, it was certainly a standard of prior editions.

My UPDATED List.  Note that this contains the components and locations of a City.  It does not list specific elements of the Main Keep or Castle, or sections of the City Wall (which I imagine as being 30 feet tops, not including watchtowers).

1. Apothecaries / Alchemists, and Jewelers (useful for both spell components, concoctions, and gifts)
2. Black Smiths, Armorers, and Weapon Smiths
3. Astrologers (though likely better suited and attached to Noble Houses and even Royalty)
4. Two Primary Houses of Worship (because conflict is fun), along with lesser shrines scattered throughout the Town / City
5. An Orphanage
6. A Fightclub, either a full on Coliseum or something more underground.  Maybe a place for bear baiting and dog fights?  Groups comfort will definitely come into play (with the animals of course, because screw the humanoids)
7. A Graveyard (one inside the walls for people of note, and one outside for the commoners and riffraff (possibly including mass graves for paupers))
8. A Brothel or two (depending on the maturity rating you associate with your Campaign)
9. A Guards Barracks
10. Guild Halls for Carpenters, Roofers, Glassmakers, Haberdashers, Tailors, Cobblers, Weavers, and Stone Masons
11. Wine Makers and Millers should be outside the city walls but relatively close by
12. A full on street plus for food shops and stalls
13. Puppet Shows and Actors Theatre
14. ”Public” Pools, only available to those with Class, Wealth, or by Invitation
15. A Bank or three
16. A Library (although depending on how true to history your game is, that is likely something available only to Nobles and Royalty and part of their estates).  Alternatively, there actually COULD be a university, I sometimes forget that these wouldn’t be super anachronistic.  Even GRRM had one in his series.  They also started cropping up at the end of the Middle Ages, IIRC
17. Multiple Inns and Taverns
18. Slums
19. Jail, Pillories, Gallows
20. Loan Sharks
21. Pawn Shops and Book Stores
22. An Auction House
23. Stables and Warehouses (dry goods, building materials, shipments)
24. Breweries (in the city?)
25. NO Thieves Guilds, criminals do not advertise
26. And an obligatory anachronistic sewer system, lmao

Farms should be a distance away outside the walls, requiring the farmers to cart their food stuffs into the city.  Make sure there are bailiffs on the gates checking carts as they come in.  Obviously everything here doesn’t include regular houses.  If there are places for public parks or gardens, great, otherwise confine those to the Estates of wealthy merchants, nobles, and whatever royalty may exist.  Don’t confine yourself to straight lines for streets, and create small intricacies of architecture such as an arching bridge that connects to a lane while crossing a street below.  Fountains and Statues might start to appear in the wealthier neighborhoods.  Musicians will play for coins at taverns and on street corners.  Dice will be the most common form of gambling but cards are not so rare that a game can’t be found in the better dens.  Numerous wells if there isn’t a freshwater source nearby.  There should be a nearby estate with large woods for hunting that the local lord makes available to his liege.

I want to thank our OP for this, by the way.  I’m in the early stages of designing my own homebrew and after the first dungeon they’ll come to a large city which I would love to incorporate as many of the above as I can.  I’d imagine it as my world’s version of Kingslanding / Oldtown from Game of Thrones, or Novigrad from the Witcher (especially The Witcher 3).

I’ve DMed several times, and I usually try out things I loved as a player. One such thing is contests. At various festivals or holidays, people can hold contests. Perhaps there is a street hustler that can play a game with a PC. I’ve done pie eating contests where you make CON saves to stay in the game, as well as a pig herding contest, with several animal handling checks required of sufficiently difficult DC to here a bunch of pigs into a pen. You can offer simple magic items, such as a Cloak of Billowing or something like that. If you don’t want any magic, then gold is also a fine prize for winning contests.

Seasonal events

Yeah Magic Item Shops would be very rare, and definitely only in those aristocratic regions in cities. Perhaps maps to rumours of possible magic items could be sold instead?

Another thing I’m curious about is what kind of landscapes people might like to place their favorite cities on.  A hill or hills with maybe a river or river running between the city or close beside, the ocean/sea not so far.  The main castle on a cliff outcropping (not right up against the edge with just a narrow strip between the walls and an insane drop off, but close’ish by) with the city itself spreading out below and the sea nearby (can’t go wrong with port side cities).

I place my towns and cities on the ocean or on the rivers.  Even today, the vast majority of the world's populace is on a body of water but this was even more important in ancient times when water were the only "roads" in existence.  

My favorite city I have created is Riverfast, modeled after Koblenz, Germany.  Two rivers come together ("Deutches Eck" in real life) and the town is at the center of the Y.  Fields are on the E bank of the main river (The Rhein in real life), which is filled up with river silt (like the Mississippi delta in my state).  Hills to the west and Dark Pine Forest (Schwarzwald in real life) to the south with a druid enclave. The trees are so large and thick they block out the sun.  The main river runs north, eventually to the sea and a trading town.  The west river bank is terraced for grapes, which are turned into wine. 

My new city is going to be on the Eastern coast of a very West European Continent.  I imagine a (size unknown) River, snaking down from North Northwest through the city, almost bisecting it before flushing out into the sea to the east and below the city.  I loved those two long lists Appellion (?) made and will be using or even adding in to them.  The city will itself be bordering the coast, I’m just not sure how close.  I like the idea of the Castle being on a craggy promontory overlooking the sea, I’m just having trouble matching my vision to the paper.

A Nightmarket. Somewhere below the town in derelict cellars and/or connected corridors (old mineshafts or part of a stormdrain or cisterns, or just old ruins that have been built over and forgotten) a market for stolen or illegal goods, but nicely lit up with colorful stalls etc.

A fairground.

Way back when, there was Citybook, and not too long from now will be a new third party book from Jennel Jaquay. 

Generally speaking, I keep cities as low key as possible, with fairly atypical setups that are particular to the cultural place. 

That said, I do have small, winged monsters that are fond of dark alleys and petty thievery, and lots of cultural objectification and discrimination that tends to provide a goodly bit of potential conflict, as well as stuff like some magic being illegal (and laws being inadequately enforced).

That said....

I was an early adopter of the kinds of things I mention in the first line. I create different people and give them personalities and quirks for all manner of things, and then drop them into the different locales.  Cities are different from Towns, towns differ from villages, villages are different from hamlets, and so forth.  But I am also someone who deals with that stuff "in real world" terms, so it leaks over. 

I don't do a lot of "in settlement" adventures. Players sometimes decide to ignore what I have set up, though, so it becomes a lot more fluid as needed, and for that I simply play it straight -- what does a hamlet of a couple hundred folks do when a group of powerful folks shows up? A town of a couple thousand might be a little more involved, but also the local Feudal ruler may have some quirks.

And nearly all of it is spur of the moment.

Here's a few ideas that might or might not have been mentioned already:

*  An impeccably clean wishing well that seems to be able to respond to the PCs.  Actually, a Nereid is enslaved and responsible for cleaning the well every few hours. The nereid has been trained to listen to people in order to be able to collect more coins, below a certain daily amount and she gets punished.

*  (Illegal?) Fighting ring. Probably a centerpiece of the slums. People gamble on who wins.  There's rules, of course, which the PCs or NPCs might try to cheat at.

*  Quarantine center: An infestation of higgledeepuffs or whatever Tiny sized magical critters have been raiding the local farmers. Any suspicious looking familiars (including invisible ones), magic items, pets, etc. are inspected thoroughly.  A few of the inspectors are likely to be rude to the PCs, perhaps trying to rile them up.

 * A museum of dead princes who tried and failed to rescue the princess from the 100-foot tall tower just outside of town. The princess is long gone, but at least the town has a macabre tourist attraction it can boast about!  If the PCs pay the admission fee, they might just find a useful or item or two they can attempt to steal.

*  The private zoo of a noble family or retired investment mogul. Naturally, the zoo contains some rare Monstrosities that happen to escape while the party is in town.  If you want to put a more thought-provoking spin on this, make some of the Monstrosities sentient and have the party decide whether they would rather get paid to return them to the zoo or to set them free (with the concomitant risks of being killed by other nearby Monsters or recaptured).

I like the zoo idea, it’s a good reminder of traveling attractions.  I remember from various books showmen presenting a monster of one sort as another, that kind of thing.