The Shambles is the oldest and most densely populated part of the city. Many of the building still exist from the early parts of the third age, constructed by Goblin slaves. The Shambles is well named, full of twisting streets and blind alleys. The Shambles lies on the banks of the Tooze, from the Docklands north.

There are several taverns and inns in the Shambles. Most are of good quality, but are frequented by members of the Shadow Guild. The Magic Helmet, at the eastern end of Fog Lane, is a good quality tavern with sensible prices and wares. The best in the Shambles is The Harpy’s Spear, lying at the crossroads of Blackberry Way and Penny Lane. This tavern boasts some of the finest beer and food in the city, easily on a par with The Chalice and Bracer.

In the twisting lanes of the Shambles there are many shops and stores, far too many to be mentioned here. There is one worth a mention though. Four Paladin’s Forge can be found outside Saddler's Wharf, just north of Eastwatch Keep. There, the dwarf Yargan Gaerla runs the best weaponsmith in Midwinter. Few outside of the Shambles know of the place and even fewer are prepared to brave the district to buy his wares.