Geography:

Oakenshield was one of the nineteen castles built by the Night's Watch along the Wall. Though it still stands, it is long abandoned.

Oakenshield stands west of Woodswatch-by-the-Pool and east of Castle Black.

Oakenshield is a ruined fort of oaken timber. There is no tunnel through the Wall at the castle. There used to be an earthen ramp to the top of the Wall, but all that remains of it now is a mound of earth three hundred feet high between the Wall and the castle.

History:

Oakenshield is the second youngest castle on the Wall, with only Deep Lake being newer. The castle as it is was never intended to be permanent, but as a temporary redoubt to give shelter to the men who were building the permanent fortress of stone. But one mishap after another plagued the construction site until, hopelessly stymied, the Watch gave up on building in stone and made fast their wooden keep.

The work on cutting a tunnel through the Wall at Oakenshield had only just begun when the orders came to leave. The earthen ramp that led to the top of the Wall was undermined and collapsed when the black brothers abandoned the site.

Recent events:

King Stannis I Baratheon inspects the ruins of Oakenshield.

When the wildlings led by Tormund Giantsbane are given age through the Wall, Lord Commander Jon Snow gives Tormund Oakenshield as his seat, to keep him close at hand. Tormund brings his own folk (including his son Toregg) to settle Oakenshield within a day or two of arriving at Castle Black. Bowen Marsh, the First Steward, points out that with Tormund at Oakenshield and Morna White Mask at Queensgate, they have foes on either side who could easily cut them off from the rest of the Wall.

When news reach the Wall of the dire situation at Hardhome, Toregg promises Leathers that Tormund will bring eighty fighting men from Oakenshield. Tormund ends up bringing only fifty, however.

Current garrison:

Commander of Oakenshield: Tormund Giantsbane

Second-in-Command of Oakenshield: Toregg the Tall (presumably)