Flashback 1926: Milson’s Point homes and businesses demolished for the Sydney Harbour Bridge.

WINE SHOP + BUTCHER: 67 – 69 Alfred St.

Wearing a waist coat and tie, the dapper man leaning against the post outside 67 Alfred St was likely Thomas Bourke, the owner of Milsons Point Wine Shop. Zoom in and you can see a neat display in the front window, with Caldwell’s wines taking pride of place. A fashionable brand in the 1920s, Caldwell’s Muscat or Port was the chosen tipple for men, with ladies often drinking socially acceptable Sweet or Dry Sherry.

Another man, wearing a striped apron, looks directly at the photographer as a woman enters the shop next door. Perhaps he is Mr W Dale, owner of the Butchery who sold prime Ox tongues, choice veal and “high-class meat”.

LAY’S MOTOR GARAGE: 87 – 91 Alfred St.

With more cars on the roads after the Sydney Harbour Bridge Act was passed in 1922, the enterprising Lay brothers thought Alfred St would be the perfect site for their motor garage, offering a full range of car sales and services.

Open day and night, the business recharged batteries, hired cars and filled petrol tanks for 2/4 pence from a “Guaranteed Shell” pump at the front of the service station.

By the end of 1926, the brothers were selling up and moving out after their land was resumed, offloading assets including a nearly new Ford 1-Tonne truck for £140.

CORNER STORE + HAIRDRESSER: 79 – 81 Alfred St.

Dressed in a suit and tie, a man leans on the windowsill of a grocery store, as a young girl and her dog wait at the entrance.

Perhaps the trio have accompanied the woman you can faintly see inside, who may be picking up some ingredients for dinner. The shop was owned by Ernest Clayton, who worked hard to build up his small business on the corner of Alfred and Fitzroy St.

Next door, Mr O’Connor runs the local Hairdresser and Tobacconist, offering ladies and gents cuts in a “hygienic saloon”, where children’s haircuts were a specialty.

DINDS HOTEL: 83 Alfred St.

William Dind was a well-known man of the arts who ran the Victoria Theatre in Pitt St (where the Strand Arcade now stands), before heading across the harbour to become a publican in the early 1900s.

His hotel soon became a popular meeting place for the “theatre set”, with its walls adorned with magnificent portraits of stage celebrities.

“Along with the actors and actresses came many legal and literary men, who “dined and wined” in that North Shore inn,” the Daily Telegraph reported in 1923.

NEWSAGENCY: 53 Alfred St.

Mr A.J Gardiner ran the Milson’s Point newsagency at 53 Alfred St, selling major mastheads like the Sydney Morning Herald, the Sunday Times and the Evening News. The enterprising local businessman also ran the Milson’s Point Circulation Library along with stationery and tobacco.

In the decades before suburban libraries would become commonplace, hundreds of ‘circulating’ or subscription libraries operated in Sydney. Mr Gardiner’s service allowed residents to “rent” books for a small annual – or quarterly – fee.

REAL ESTATE AGENT: 77 Alfred St.

Compton’s “Mutual Business” Agency leased houses, flats and single rooms for local workers from 1916 until it was demolished, shortly after this photograph was taken in November 1926. The small office, wedged between Mr O’Connor’s Hairdressing and a Grocery store, relocated to Glen St in 1927.