In 1829 he leased part of his land to William Cross who was licensee of the nearby White Hart Inn, one of the earliest licensed premises in the colony.

[1][3] Convicted London joiner and carpenter James Gough (1790-1876) who arrived on the Earl Spencer in 1813 and got a conditional pardon in 1821 won a private commission for the White Hart Inn between Parramatta and Windsor.

[1] During the 1840s depression Booth found himself in financial trouble and his creditors foreclosed on his property, selling it to George A. Sheffield in 1852.

He also purchased the license and additional lots adjoining Davis' original holding to the north and east of the property.

[1] In 1962 Windsor Road was realigned, widened, straightened and sealed, and appears to have been the impetus for Binns to subdivide the inn site into at least five allotments under deposited plan 30916.

This has allowed the construction of the rear machinery shed to form the Vinegar Hill Woolshed in 1985 and a Wedding reception hall to the northeast of the old inn in 1986–87.

[5][1] Single storey Georgian sandstone inn, with front verandah and a single-pitch (formerly tiled), hip roof over the whole.

Front six-panel door has glazing in the upper four panels, flanked by side lights and surmounted by a large fanlight.

[1] The building has stone cellars below, and sandstock brick extensions to the rear (south-eastern end of inn building) on a lower ground level (originally a kitchen, possible smoke house/ meat preserving room, high roofed open sided area possibly for carriage storage, and large room with a baker's oven, then an attached blacksmith's shop built of timber slab.

[1] As at 5 January 2012, historical evidence suggests that the major physical development of the site was focused on the Windsor Road frontage and specifically the position of the first Inn.

The archaeological resource is likely to exist in the form of disturbed occupation deposits within the footprint of the Inn and rear extension.

The potential archaeological resource away from the main Inn complex had been severely disturbed by development of the site, especially grading works associated with the carpark.

The Inn is a significant component in Windsor Road's urban landscape, representing a site important in the development of early travel routes in the colony.

The historical development of the site reflects the changing nature of roadside inns, particularly in response to the increase of rail travel following the construction of the railway line.

[1] The inn is indicative of an era when such buildings were used as resting places and watering holes between Parramatta and Windsor prior to the construction of the railway line and played an important role in the economic and social development of the local area during the nineteenth and twentieth centuries.

[1] The place is important in demonstrating aesthetic characteristics and/or a high degree of creative or technical achievement in New South Wales.

[1] The place has potential to yield information that will contribute to an understanding of the cultural or natural history of New South Wales.

[1] The place possesses uncommon, rare or endangered aspects of the cultural or natural history of New South Wales.

The Fiddler has State significance for its ability to represent an important class of traveller amenities once common on the early road system of NSW.