We can’t be sure what Woodford Academy – the Blue Mountains’ oldest building – originally looked like in 1834. We can however get some idea from a detailed sketch made of the property eight years later in 1842.

Following Thomas Pembroke being granted a liquor licence to operate at Twenty Mile Hollow, the way was clear for him to construct a ‘well built stone and wood house on the roadside known by the sign of The Woodman.’

At the time that Pembroke sold the property in 1839 the inn comprised ‘nine excellent rooms, stabling for six horses, store, stock and sheepyards with a productive garden and an overflowing spring of pure water.’

1889

The additions which added the second storey loft to the western edge of the building date back to the late 1850s when the inn was run by the Buss family.

The prominent line of first floor rooms we see in the sketch left from the London Illustrated News, shows how the property was adapted in the early 1880s to its new role as a guesthouse.

Between 1907–1925, these rooms provided the dormitory accommodation used by students boarding at the Woodford Academy.