The first North Gregory Hotel was built by Corfield & Fitzmaurice in 1878, and legend has it that on April 6th, 1895, it was the site of the first public performance of ‘Waltzing Matilda’. The Hotel has been destroyed by fire three times, the latest in 1946.

In 1950, the member for Gregory, Hon. G.H. Deveries, MLA, piloted a bill through Parliament enabling the Winton Shire Council to own and operate a hotel. Subsequently, the Hotel was reopened in 1955, built around the same time and by the same architect, as the Winton Shire Council Office and Memorial Hall. The Hotel was sold back into the private sector in 1989.

Sand-blasted doors grace the Hotel, depicting the story of Waltzing Matilda and pastoral scenes, created by celebrated Australian artist Daphne Mayo.