The Dog and Duck Inn George Street Brickfield Hill
  The Dog and Duck in 1842 stood just up from the Toll gates leading onto Parramatta Road.

Hope and Anchor was the first Inn, then Wheatsheaf, then the Dog and Duck  Each inn stood on around 3 acres of land. Joseph Collets was the Licensee in 1836 holding the Inn while Thomas Higgins was trying to find a new Leasee.

 

Christ Church (left), c 1850, before the construction of the spire in 1855/6. The buildings to the right are the Sydney Turnpike and the Benevolent Asylum.

Christ Church, c 1880. The "old round house" stands at the apex of Pitt and George Streets. Source http://www.ccsl.org.au)

The Toll gates were operating until 1842 when the tolls  moved to Annandale and then totally demolished in 1850 and replaced with the police watch house, referred to (inexplicably) for many years as the "old round house" was completed in 1856. It stood at the apex of Pitt and George Streets immediately to the south of Christ Church and consisted of a keeper's room, guard room, inspector's office, five cells and two exercise yards (one for men and one for women). It was demolished in February 1905.

 The Dog and Duck Inn  faced the Police Watch house  for 40 years until  the Inn was demolished in 1896.

Sydney turnpike

The Sydney Turnpike 

 The gothic-style Sydney turnpike. The Benevolent Society's Asylum
is pictured to the right.

The Sydney turnpike sat at the apex of Pitt and George Streets, just to the south of Christ Church. Tolls were charged for the maintenance of the roads. It consisted of a gatekeeper's lodge (positioned at the apex of the triangle) with gates extending across both George and Pitt Streets. It was designed, in gothic style, by convict architect Francis Greenway in 1819. It was demolished in the 1850s to make way for the "old round house".

The expansion of Sydney was marked by the relocation of the Sydney turnpike (on the Parramatta Road) to 100 yards (91 metres) short of the Annandale boundary, Johnstons Creek, around 1842.

 

Benevolent Asylum

Benevolent Asylum 

The Benevolent Asylum was erected on Pitt Street, near the corner of Devonshire Street in 1820 under the patronage of Governor Macquarie. It was officially opened on 12 October 1821 and was operated by the Benevolent Society of New South Wales.

It was demolished in November 1901.

742 George Street, where today the Capital Terrace Stands