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The Observer Tavern was constructed in 1848 as a two storeyed, six room public house. The tavern was owned by Robert White from 1847 till his death in 1875, after which the hotel was managed by his trustees, Benjamin Palmer and Thomas Moore. The land was resumed in 1901 under The Observatory Hill Resumption Act, 1900.
In 1908 Tooth and Co. purchased the site and held freehold title. The Sydney Cove Redevelopment Authority resumed the land in 1977.
Rumour abounds that the hotel has its own resident ghost, which is said to be the spirit of a woman murdered by the then republican, N. Grindall, in 1944.