When The Willoughby Hotel opened its doors for trading in May 1899 it was one of the outstanding landmarks of the north shore – a striking Italianate structure with sweeping 360 degree views. From the verandah you could see west to the Blue Mountains, south to Botany Bay, east to the Pacific and north over a vast expanse of untouched bushland.

The hotel was built by the brewer, Tooth & Co.Ltd, as a “tied” outlet for its products, with the original lease being taken up by James Smith.

In 1901, Joseph Knight Smith, recently returned from “active service for the Empire during the South African War” purchased the goodwill of the h otel, and it was to flourish under his management for 27 years.

The hotel had a strong residential trade with forty rooms for guests. Visitors from the city frequently spent weekends or other breaks at The Willoughby taking bushwalks or relaxing on the hotels lawns. Norman Lindsay was a frequent guest at the hotel. Knight Smith’s hotel was self sufficient in many ways, with its own vegetable gardens, poultry and cows.

The Suburban Herald in 1926 was rather lavish in its description of the hotel, extolling the "brightness and glitter of the island bar, exquisite taste of the murals, the luxury of the lounges, beauty of the adjoining conservatories and evidence of refinement and culture in the appointments in the guest rooms."

Knight Smith bought the adjoining “Assembly Hall” in Penshurst Street in 1920 and converted it into a billiards hall with Heiron & Smith tables. The name “Knight Smith Building” remains above the awnings to this day, although the billiards hall is long gone.

Knight Smith was a pillar of the Chatswood/Willoughby area, and served as an alderman on the Willoughby Council. In 1926 he actually supported actively the establishment of a new hotel in Willoughby on the grounds that it was needed for the rapidly expanding area . That hotel is the Bridgeview in Willoughby Road.

We are fortunate to have much of the correspondence between Knight Smith, as lessee and Tooth & Co., as lessor, from his time at the hotel.

It’s interesting to note that for much of the period Knight Smith used the address “Middle Harbour Heights” instead of “Willoughby” on the hotel’s letterheads.

There have been several long term Licensees of the hotel, following Knight Smith. The Walsh family purchased a lease in 1936 with Patrick Walsh as the Licensee.

In 1947, the lease was transferred to Kevin Ryan, son in law of Patrick Walsh, who was to remain the licensee for nearly 30 years. It was during his term, in 1956, that Tooth & Co. made the only addition to the original hotel building – a lounge with entry off MacMahon Street. This is now ”The Blue Room”.

In 1975,the former great Kangaroo second rower, Brian Hambly (South Sydney and Parramatta Rugby League teams) bought the lease and remained at the hotel until 1979. Brian was a popular and successful publican and made many changes to the hotel.

The next long term Licensee was Joe Sands, who bought a lease in 1986 and then in 1989 was a member of a syndicate which acquired the freehold from Tooth & Co. Ltd. The brewery had owned the property for 90 years.

The Blamey family, with Scott Blamey as Licensee, purchased the freehold and business in November 1997.

In late 1998, a major refurbishment of the hotel began. This huge job included the construction of a replica of The Willoughby’s original verandah which had been replaced by a standard pub awning. Heritage architect, Kevin Riggs, worked from old photographs to establish the dimensions of the verandah and work was completed in late 1999. (The original verandah was demolished around 1917 apparently because of white ants).

The Willoughby City Council recognised the restoration of the hotel with a special Heritage Award in 2000.