Just behind the visitor will be the foremast, and the OLYMPIA's pilot house. The entrance to the pilot house is on the starboard side of the structure. The pilot house is made entirely of wood. The present pilot house is slightly larger than that originally which originally existed on the vessel, being enlarged in 1901. The space is still quite small, but houses the main, large ship’s wheel, two engine order telegraphs, a magnetic compass, a chart table, and a bunk for use by the captain as needed. The pilot house even contains what was, at the time of the Battle of Manila Bay, a new marvel – a direct-line telephone for communication with the captain’s stateroom.

Normally, in times of battle, the command of the vessel would be shifted from the exposed pilot house to the protected conning tower. Dewey, however, maintain the command at the pilot house. The ship's wheel in the pilot house was used during the Battle of Manila Bay.

Atop the pilot house is another open bridge, with a voice tube leading inside the pilot house. At present, there is no access to this level.