Personally, one of the hardest things for me in a setting is players hanging out in the city and asking what shops are around. TankHammer actually does a lot of this for me because he's both good at it and enjoys it, but not everyone has as awesome a friend as I do. So, I thought this might be a fun game for people: Post an establishment that could fit in most D&D cities so that DMs have a place to go to grab ideas while running campaigns.

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Riverbank Inn - One of the largest inns in the city sits right on the waterway with half the rooms overlooking the river and most of the others over the roofs of the neighborhood due to it being a good 2-3 stories higher than most buildings in the district. The eye-catching green roof also helps make this a city landmark for out-of-town travelers to find their way around. While the business is actually owned by one of the city’s wealthy merchant class there are also a handful of on-site managers and dozens of staff. The ground floor houses a restaurant, tavern and lounge rooms in addition to a front desk. All of the employees wear the signature green and silver-trim uniform while on the job.

Mint Street Fashions - This 150-year-old clothing shop has been at this location just a block from Merchant’s Row since its founding, though it has gone through several owners in that time. Its current proprietors are Fiona and Mahal Odinson, a husband and wife partnership. Mahal handles most of the alterations while Fiona runs the day-to-day business and sales. Their teenaged daughter Sophia began working the shop last year when she turned 13 and has made an impression on the clientele with her sharp eye for color.

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~SE++

The Singing Anvil

Owned Balthos Bronzeweaver, a stocky dwarven craftsman who works as the smith in a small town with a couple of human apprentices. He has thick auburn hair and a chest length beard which is forked into two large braids which are frayed and frizzled at the end. He doesnt worry much about his appearance and is frequently caked in grime and soot from head to toe. He'd be happier forging weaponry, but is content crafting picks and shovels and other such equipment needed for the townsfolk and spending his time laughing over a mug of ale with a pipe of tobacco. Despite his often filthy appearance he keeps his shop and work benches pristine and can sometimes be heard scolding his apprentices for leaving a tool in the wrong place or something similar. He wakes each day with the dawn and soon begins preparing his shop for the days work.

That looks like Old Tristram.

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Bless the Wall Tavern - Set up next to a long-standing temple at the western edge of the city. During the late afternoon the outer wall's shadow stops just shy of the front door of both buildings. There are a few rooms to rent by the hour in a smaller, annexed building.

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~SE++

The Lucky Scoundrel

The inn is a single story stone-walled building, with a slate roof. The sign shows a grinning man raking in coins from a winning hand of cards. A collection of weapons hangs over the hearth. Accommodations consist of several small rooms with beds and woolen mattresses.The innkeeper is a short female elf named Bouda who enjoys working at the inn and chatting with the local townsfolk as well as traveling traders and adventurers.

Menu
Braised Grouse with Garlic and Dried Olive, Glass of Brandy
Dried Shellfish and Lettuce, Tankard of Mead
Poached Eel and Mulberry Tart, Glass of Whiskey
Salted Grouse and Buckwheat Bread, Tankard of Ale

Common Patrons
Burga: Female Human Soldier, Good. Burga has curly auburn hair and bright gray eyes. She wears chain mail and wields a bardiche. Burga compulsively plays with her hair.
Khali: Male Dwarf Merchant, Neutral. Khali has copper hair and amber eyes. He wears simple clothing and a wide-brimmed hat.
Bryne: Female Human Trader, Good. Bryne has blonde hair and brown eyes, and a distinctive scar on her arm. She wears well-made clothing and riding boots. Bryne is courteous and inquisitive.
Jastor: Male Halfling Scholar, Good. Jastor has silver hair and sharp amber eyes, and a flat nose. He wears modest garments and an amulet of luminous crystal. Jastor is well-spoken and virtuous.

Reddick and Associates Acquisitions

This wooden single-story building squats in the middle of a lonely road in one of the cities more disreputable districts. Though the front window opens onto the street the entrance to the store itself is located down a side ally, illuminated at all hours by a flickering lantern. Looking through the window or entering the store provides little clue as to it's intended function. The building is filled with all matter of detritus; old books with frayed covers, moth-eaten items of once fine clothes, lightly-damaged furniture, racks of blunted weapons and display cases filled with obviously costume jewelery and unlabelled vials of mysteriously coloured liquids. Almost everything is covered in a thin layer of dust. In fact the store only seems to be frequented by shifty-eyes men who quickly disappear down ally ways after noticeably not purchasing anything.

The store serves as little more than a front for Reddick's actually business; his 'acquisitions'. For a considerable fee Reddick and his associates guarantee to be able to track down the location and enact the recovery of any item 'lost' within city limits. Such activities have not gone unnoticed by the city guard and raids on the business are frequent but always come up empty handed; if Reddick is hoarding stolen goods he certainly isn't holding them at his store.

Proprietors
Wes Reddick: A pale half-elf with slick dark hair, a small mustache and thin features. He wears surprisingly fine clothing and a perpetual grin. He is well-spoken and polite but says little of real value unless paid to do so. He has a notable distaste for elves, though he hides it well. He can be found in the store during it's daylight hours.

'One-Eye' Hrusk: A particularly heavy set half-orc with dark skin, a bald head and a bored expression. A thin scar runs across his cheek and left eye though it is usually covered by a patch. He wears thick studded leathers and a well-used mace hangs from his belt. He talks little and becomes visibly agitated if questions stray from business. He has a notable dislike for everyone. He can be found in the store during the night.

'The Associates': A motley gang comprised mostly of humans and half-orcs with the occasional halfling, gnome or dwarf in the mix. When not drinking themselves into stupors in the local inns they spend there time loitering in small groups in the ally ways and streets surrounding the store keeping an eye out for trouble. No matter how many the city guard drag to the stockades there always seems to be enough that there presence is felt in the area.

I very much like that one Garren. And 'One Eye' Hrusk reminds me of a character I was just playing not too long ago. A half-orc with the same eye missing that went by the name Rook 'Dead Eye' ...though he didn't wear the eyepatch and prefered that people saw the eye.

The Scoured Scoundrel

Despite the name, The Scoured Scoundrel is an upstanding bathhouse in the wealthy section of town, named as much to be a bit tongue in cheek. The floors are slatted wood and below there is a two foot deep hole under the entire building where water is pumped in and heated so the entire bath is steamed. It costs two copper to bathe in there, four if you need lye, and ten copper (or one silver if you allow silver in your world) for them to provide bar soap to be used. Decorated in deep browns of natural and pliable wood on the floors and the lower two feet of the walls, and forest greens for the walls, the bathhouse has a very calming effect on its patrons.

~SE++

By Tongue And Quill

Description
From the street the stone building is noticeably shorter than two stories but taller than one and is adorned by two smallish windows on either side of a large wooden door which is adorned with beaten brass. Above the door rests a beautiful wooden sign that bears the name 'By Tongue And Quill' all on a single line in elaborately carved yellow letters in stark contrast to the dark stain applied to the rest of the sign. Upon entering you find that you first descend several stone steps to arrive on the first floor which is a few feet below the street level outside and made of wooden planks covered with various thick rugs. Shelves line the walls and each of them is lined with books and tomes of every shape, size, and color with a layer of dust along the spine of a majority of them. Straight ahead a narrow path leads between several tables , each of which have various parchment and maps scrawled across them, to the back where a older human male sits at an oak desk. Oil lamps illuminate the room since only thin beams of light make it through the dust on the windows and around the books stacked nearly in front of them.

Owner
Jessep Gilroy, a retired adventurerer, owns and runs the curious little store selling overland maps and diagrams of various dungeons, sewers, caves and the like.

Awww

Maybe if I'm not out until later in the day tomorrow I'll throw-together some more interesting establishments.

I like the idea of themed quarters and like to think about how neighbors interact with each-other and how certain buildings, establishments and their clientele and employees interact with each-other.

Like, you wouldn't have a seedy dive-bar next to a thriving bazaar. The businesses and setting should go together like any real-life city. I have this idea about one of squinty's cities having a 'dwarven quarter' where the city runs up against a mountain or other rock-face and some of the streets become tunnels in the side of the rock and act like an indoor shopping/residential district which would lead further in to the industrial/mining district. I also enjoy the concept of ethnic burroughs in a city being applied to fantasy settings. Something like late-19th-century New York where you have immigrants establishing their own neighborhoods with their own distinct flavors and smells and festivals.

I once visited Montreal and they have an 'Underground City' there where several blocks worth of buildings are joined together by their basement levels that act as a sprawling shopping district below street level. Something like that is so cool and yet very practical in a town where you can see some seriously harsh winters.

Speaking of Montreal, a biodome would be quite a fun thing to have in a nature-loving city.

Here's some from my earlier brainstorming with squinty:

Hendel’s Under-the-Hill - A dwarf-owned bar on the rocky, mountain-side of the city run for the better part of a century by the enterprising Hendel Shale. The tavern shares its striking architectural style with the neighboring buildings which are all carved into a 40-foot-high, stone outcropping which the rest of the neighborhood bends around. A number of storerooms and living quarters extend under the expertly-carved public room but rumors persist that the proprietor has dug out more than what he shows to his clients and employees.

Defensive Measures - Often-enough one might find her/himself facing a threat of physical harm or worse. Defensive Measures is a business that understands that sometimes the best tool to avoid harm is to be the person on the street with the biggest weapon. This dwarven shop might be dimly-lit, cramped and have a low ceiling and a sometimes-hostile staff but it’s the best place to go to find a razor-edged battleaxe or a warhammer with an engraved skull on the business end. The business is owned by former mercenary and full-time smith Griswold Stonesplitter.

It's been a minute but I churned-out a few more tavern/inn type places since they are some of the most-frequented settings for adventurers.

The Yellow Pine Inn - This classic pub has been a popular stop-off for visitors 3-centuries-running. Most of that time it’s been maintained by Amorrah’li Nibenbell, a young-looking elven woman with bright blue eyes and golden hair. While her small staff take care of the day-to-day Ms. Nibenbell is usually seen flitting from one guest to another in the main room asking if they are finding their accommodations to their liking in a sing-song voice. She treats her regular customers with a very maternal manner which most simply accept without causing a fuss. The Inn itself is two-storied with three large rooms and a small pub/check-in area on the main floor while the second floor houses single bedrooms all off a single hallway bordered by a long window that looks down over the entrance.

The Foundation - This bar’s casual-yet-dignified air is diminished slightly by the eye-rollingly awful pun in it’s name. The Foundation is housed below street-level, built into the basement of a block of shops and apartments and is reached by a stairway that runs parallel to the footpath. It consists of one long, ivory-colored bar surrounded by brown and red booths and tables. The regular bartender is Bowen Drake, a short, fit human with shaggy orange hair and mutton chops. His late brother Dillon was a bow-for-hire some years ago and he’s always happy to chat with adventurers over a stein of amber when he can. The place is lively after sun-down but usually sees very little activity during the day.

The Halftower - The true, official name of this hotel is “The Bradley Castle Inn” but nobody outside of the proprietor actually refers to it by its proper name. The Halftower is a landmark on the highway due to its unique appearance as it was once built as a 70-foot stone watchtower many lifetimes ago. All that is left is about 3 and a half floors plus an addition at the base. The rest of the tower was destroyed by some magic or siege weapon a century or so ago and the half-hearted attempt to patch a roof back on top with thatch fools precisely no-one. Still, it is a solid structure with a decent view and a roof that doesn’t leak so it’s seen more than its fair share of business from travelers.

The Collector's Nest

This bartering establishment is tucked away in a back alley is know for being filled to the brim with eclectic and unconventional weapons. Whether you are looking for a Gnomish Pickhammer or Chakram, chances are you might find one. The more standard style of weapons may also be found there like short swords and warhammers may also be found here at times in lesser quantities. One unfortunate feature of this place is that the place is built with dimensions more fitting of the size of its proprietor, a yellow skinned goblin by the name of Zoresm Bomz. He is known for trying to convince his costumers to try out something unique even if the costumer knows what they want and repeating item names. He is friendly to all new costumers. Just don't ask what he keeps in the back...

Wrote Down

A small hole in the wall shop hidden down a back alley. Wrote Down is a scroll shop where mages go to purchase spells they don't have. The entire trade is done in the form of exchange plus one gold coin per transaction. When you purchase a scroll, you pay in the time to make a new scroll of a different spell. The merchant manages to keep his trade going by the small amount of gold he receives, as well as a constant rotating stock. Going in there is a crap-shoot on getting what you need, but you'll also find things you never thought you'd find there.

~SE++

This thread needs more of the oddball establishments: moneylenders, cobblers, tinkers and alchemists.

Alright, gave a bank a shot.

Nash Security and Loans - This structure may be one of the most striking in all the city. Sometimes called “the irontree building” by locals and for obvious reasons, this bank building’s upper floors balloon outwards into a metal cage which can, from-afar, make it look very much like a thick tree with a marble trunk and iron branches. The high-ceilinged main lobby is octagonal with doors opening onto the street on the north-west, south-west, south-east and north-east corners of the floor-plan and a rectangular inner structure contains the bank tellers and delivery mechanisms of the business. During a transaction a customer typically approaches one of the many tellers (up to 6 on each side) who sit behind an open window. They present a copper key tied with an identification code which both match a deposit box and the teller places it in a small basket which is pulled up on a string to the secure upper floors. After some time the deposit box is lowered by vault workers to the teller and handed over to the customer with the key. A few dozen copper are usually tendered to the bank per transaction as well as a yearly fee for keeping guard over the client’s valuables.
In regards to coin, a very meticulous system of ledgers is kept by a team of gnomish accountants which are copied and transported to smaller branches regularly around the world, thus any customer wishing to withdraw more than half of their savings typically must wait a week or more while the bankers verify they have an accurate account of his or her funds.

The Red Eye

A brothel in the luxurious upper-class housing areas, The Red Eye boasts a reputation for not only having beautiful women and handsome men ready to serve your every desire, but a wide variety of races to choose from. To get in requires a membership, which is an excessive thirty gold a month, which keeps the clientele to the most affluent of the city as well as wealthy traders who pass through and stop off. It is open twenty-four hours a day, has thirty private rooms ranging from silk covered beds to stone dungeons, whatever your tastes may me, as well as a private bathhouse, bar, and a temple of clerics ready to soothe your wounds and cleanse you before leaving.

~SE++

Rotgut Remidies

This establishment, named for its two claims to fame: hard liquor and alchemical remidies, is run by a husband wife couple of a full-blooded Orc male named Vokol-Mol and a female of questionable human nature named Zavrissa. (Truthfully a Kitsune, a race not native to the continent or DM's option if this would clash with the setting.) Customers are welcome to stop by for a drink sitting in a room decorated with dark wooden furniture, reinforced by wrought-iron, the room lit by glass tubes filled with glowing neon liquids. (Alchemical equivalent of an continual flame in liquid form. Zavrissa's specialty.) Inventory is kept in the back and any purchases are handled through menus, and anytime the item requested is not in stock an offer to craft the item is made to said customer. Past patrons say it is not uncommon for the couple to argue over what sort of drink would be best to try while waiting.

Dreams Come True

In the busy Noble's District there is a small building that looks like it doesn't belong. Inside it much like the outside, unremarkable and a little underwhelming. A wooden shack in a district full of prestigious houses and shops that flaunt their affluence. But the inside doesn't matter once the workers begin their work. All of the workers are strong illusionists, not that their clients ever attempt to break the illusions, they go there expressly for them. The patrons tell the illusionists what their deepest desires are, and the mages within make those dreams a reality, even if only for an hour or two.

~SE++

Closed Door

This is a shop that sells only locks and keys. All of the locks and keys are magical to varying degrees, but the average lock there will make the door nearly impenetrable. Run by an old Forge-master and mage who crafts the locks and imbues them with magical energies all himself. At this point, he is fairly weak, but has a huge inventory to be sold. The weaker locks and keys will prevent thieves from picking them, more average ones will make the doors five times stronger than the average, and a strong lock and key will enchant the entire wall with magical properties when locked to keep the room safe. Enchantments run from strengthening the doors to triggered spells that will assault the invaders and sometimes even kill them. No one knows what all of the sets do except for the owner, so he never took on an apprentice and runs the shop by himself.

~SE++

Talbot’s Cordwainer

This shoe-maker’s shop is a mobile business built into a caravan coach, though not often is there a donkey or two present to pull it around. The halfling cobbler Talbot Roundbarrel, a portly gentleman well past middle-age, earns a decent living servicing the surrounding towns and cities with his wares and skills. Rumors sometimes crop-up that he has an estranged wife and some daughters off in the world somewhere but most are too polite to ask.Generally his clients just drop their shoes and boots off at his wagon either on their way to run errands or on their way back and pick them up 2-3 days later better-than-new and leave it at that.