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[shadenight123]

A well-designed city can live long beyond the one-shot adventure it was created for, with enough work. This is just by opinion, but "hyper-realistic" medieval cities in a D&D setting tend to be quite bland. So you've got your charcoal smoker and your wainwright and your blacksmith and your thresher....it's realistic sure but those aren't exactly the details that excite players.

i was entitled by my players a title of "300% difficulty lovecraftian master of dungeons".
i give nightmares.
and usually people enjoy my quests because it's not mindless slaughter.
every person has a story, every story a reason. every thing a why, a cause and a connection.
pull a string and see what happens.
...
sorry, gotta master again one of my players activated a curse which makes hims a cannibalistic flesh eating monster. she's an elfic mage who just is going for the closest meat-sack circling around...luckily it's three in the night.

[klingon13524]

The medieval law system usually didn't use prisons. Torture and release was much cheaper.

[nenjin]

There were plenty of political prisoners however.

[Zrk2]

There were plenty of political prisoners however.

All locked up in towers.

[scriver]

I can't believe nobody has said bath houses yet. They were practically one of the corner stones in medieval society. From just basic houses with large wooden vats for the poor, to more extravagant, more lounge-like facilities for the rich and bourgeois where they could hang out, relax (do whatever upper-class drugs your setting has) and/or talk business in a friendly atmosphere. Perfect setting to meet with important personalities and the like.

The medieval law system usually didn't use prisons. Torture and release was much cheaper.

While not prisons as we know them, they did have "prisons" where they kept their sentenced-to-work workforce, as well as jails to store people before receiving whatever punishment was meted at them.

[Vector]

Read Discipline and Punish.

[olemars]

Around here they just banished people to toil in the northern wastelands.

[Virex]

Damn, that's a lot of ninjas!

You can have a wastewater drains running in the middle/on the sides of paved roads, no drains at all if streets are unpaved, or a sewer system if you're aiming for a later medieval feel and the city is rich. Keep in mind that quite a number of cities did without sewer systems until late into the 19th century.
You need a town hall, a parish church/cathedral(or whatever is the religious equivalent in D&D) and a market square(not necessarily of square shape), usually around the fromer two. You can have a permanent market hall if you want to, usually housing the richer merchants' stalls - e.g. cloth, spice traders.
Have some medieval-style industry - breweries, tailors, blacksmiths, weavers etc.
Remember to include fortified gatehouses or barbicans by the entrances to the city.
Housing and manufacturing can extend outside city walls(poorer ones most likely).
Have a few wells and maybe an aqueduct-style lead pipe system connected to a nearby spring.
A brothel is a must.
If by a river(which generally shouldn't be used as a source of drinking water, but certainly would be used as a sewerage outlet), make sure to include a river port. If by a sea, have a proper harbour and a shipyard, with forts guarding the entrance.
A library in a medieval city seems rather unlikely.

And seriously, as nenjin said, don't do "<Generic D&D Class>s' Guild". That's just cheap and boring.

A somewhat largish city typically had multiple churches, one main church in the center of town for festivities and special events, and smaller local churches catering to the districts. Also, for large towns you typically have multiple dedicated market areas, such as a fish market, a potters market, a clothes market et cetera. Also, for a somewhat comprehensive list of medieval professions, see this site. Note that there were very few factory type businesses in the Middle Ages occupied a lot of people, meaning that a significant part of the houses in a medieval city held workshops or were farms (there were quite a decent amount of farms within the walls of most towns. They weren't exactly crowded after all). See also this for more information about medieval towns.

[Max White]

see this site

Holy bookmarked that is a goldmine.

[Virex]

It's part of the magic jar project, a fairly exhaustive investigation into what makes a fantasy world tick.

[Max White]

It's flavouriffic!
Mafia subforum is going to have a freaking field day.

[zehive]

You wouldn't find a sewer.

no sewer system?  the romans had them, right? for medieval cities weren't they those small dugged channels in the center of the roads?

no sewers, and lots and lots of church. your sewer is wherever you crouched down. the only nice parts of medieval cities were where the merchants and nobles + the lord lived.

[Jopax]

I can't believe nobody has said bath houses yet. They were practically one of the corner stones in medieval society. From just basic houses with large wooden vats for the poor, to more extravagant, more lounge-like facilities for the rich and bourgeois where they could hang out, relax (do whatever upper-class drugs your setting has) and/or talk business in a friendly atmosphere. Perfect setting to meet with important personalities and the like.

The medieval law system usually didn't use prisons. Torture and release was much cheaper.

While not prisons as we know them, they did have "prisons" where they kept their sentenced-to-work workforce, as well as jails to store people before receiving whatever punishment was meted at them.

Pretty sure only the Arab part of the old continent had bathhouses.

[nenjin]

That site is a nice find. Will have to delve into the project later.

[scriver]

No, cleanliness was rather important during medieval times. In Sweden, for example, washing was considered important enough to name one of our days (Saturday, if you're curious), and people from all classes enjoyed it. They ended up outlawing the bathhouses during/after syphilis epidemics, though, as they were also a common place for prostitutes to hang around.

Basically, it was very common in Europe during the middle ages (though in the "Roman" parts the tradition ceased after Christianity took over, it's hypothesized that the Crusaders encountered bathhouses in the east and brought back and rekindled the bathing culture), they didn't stop doing it until the 16-18th centuries.