A block southeast of the city museum is Skagway’s oldest building, Moore's Cabin. Captain William Moore and his son, Bernard, built the cabin in 1887, when they staked out their homestead as the founders of the town. The NPS has since renovated the building and, in doing so, discovered that the famous Dead Horse Trail that was used by so many stampeders actually began in the large lawn next to the cabin.

Adjacent to the cabin is the restored Bernard Moore House, which features exhibits and furnishings depicting family life during the gold rush.