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History of Sydney Grammar School, St Ives

By Alec Smart

The history of Sydney Grammar School starts in 1954, as St Ives Sydney Grammar Preparatory School, when St Ives was transitioning from a fruit-growing farming district into a suburb.

St Ives Sydney Grammar Preparatory School in 1956

St Ives Sydney Grammar Preparatory School's first headmaster, Roy Dent, with students, 1956. Photo: SG Archives

But why was a site in St Ives chosen for the school, then isolated from public transport and surrounded by orchards, when other private schools in the region (eg: Knox, Ravenswood, PLC, Barker) established themselves along the main North Shore line rail corridor?

To best answer that we need to wind the clock back a century, when Sydney Grammar’s main school in the city opened alongside Hyde Park, a public common in what was formerly swampy marshes and an Aboriginal ceremonial conflict site.

Hyde Park, the first public park in Australia, and named after the London Hyde Park by Governor Macquarie in 1810, was a military parade ground, horse racing track, sports arena, kids’ playing fields and the site for Sydney’s main cricket ground until the SCG opened in 1868.

In 1832, its eastern boundary, College St, where the school’s main campus is situated, was built.

St Ives Sydney College in 1840

Sydney College c1840 on College St, Darlinghurst, the eastern edge of Hyde Park. Painting: Edward De Sauty

Imposter Headmaster at Sydney Grammar School

Prior to this, the forerunner of Sydney Grammar, the Sydney Public Free Grammar School, was opened in 1825 by emancipated convict Laurence Hynes Halloran on the corner of Philip and Hunter streets in the city (which closed a few years later, with Halloran mired in debts).

Sydney Grammar’s archive states: “The fact that Halloran had been able to establish a School in Sydney is remarkable, considering his turbulent past. Sentenced to seven years of transportation to New South Wales from England in 1819 for repeatedly impersonating a clergyman, forging testimonials and currency, he was declared “an imposter of the most dangerous kind”. His past further reveals he also murdered a man with a sword after being challenged for a trivial interference while serving as a tutor in the Royal Navy in 1783.”

However, Governor Lachlan Macquarie, the fifth Governor of NSW (1810-21), championed Halloran’s educational skills. A strong advocate of elevating the social standing of skilful and entrepreneurial former miscreants, he declared Halloran was “by far the best and most admired instructor of youth in the colony.”

Sydney Grammar School students in 1956

St Ives students enjoy drinking milk, 1959. Photo: Roy Dent / SG Archives

Sydney Grammar Hyde Park headquarters

Sydney Grammar School, a private, non-denominational education establishment in central Sydney, opened on 3 August 1857 in the ‘Big School’ on the east side of Hyde Park, on College Street, Darlinghurst.

The foundation stone of the historic Big School building was laid earlier on 26 January 1830 when it was purpose-built to house Sydney College (hence why the address is in ‘College’ St), which closed in 1850, a casualty of the 1840s economic depression.

In the years between the College’s closure and Grammar’s tenure, the University of Sydney temporarily occupied the premises, which consisted of a large main room with smaller classrooms in the basement.

Unlike many schools, Sydney Grammar School was founded by Primary Legislation in the NSW Parliament, known as the Sydney Grammar School Act 1854 – meaning serving ministers in the NSW Government voted on a Bill to bring it into being.

According to the school’s history webpage, “Sydney Grammar School was founded by Act of Parliament in 1854, after Sir Henry Parkes, the Father of Australian Federation, tabled a petition from a group of citizens concerned that the fledgling University of Sydney should have a ‘nursery’ to provide it with well-prepared undergraduates.”

The big School campus in 1920

The 'Big School' on College St, Darlinghurst, c1925. Etching: George Marler

Thereafter, in 1856, the Big School building and surrounding land was acquired and over time developed and expanded into the modern school site. University of Sydney (founded 1852) relocated to its purpose-built new site in Camperdown in 1859, the former Grose Farm, and Sydney Grammar became a ‘feeder’ school to the university.

Amidst the orchards

Sydney Grammar has two preparatory schools, St Ives and Edgecliff, the former preceding the latter by two years.

In Sydney Grammar’s online archive, the St Ives chapter reveals, “Grammar’s first preparatory school opened on 9 February 1954, under the Headmastership of Mr Roy Dent, formerly Senior History, Geography and Economics Master at College Street.

“By June, 85 day boys were attending the school and it was declared a huge success. The second stage of its development was to build several dormitory blocks designed to take up to 30 primary level boarders, an assembly hall and other necessary additions. Unlike its counterpart at Edgecliff, St Ives Prep had a wealth of surrounding land previously being a site for citrus orchards of around 14 acres.”

2075 magazine has previously written about one of the neighbouring orchards. A row of 18 historic pear trees of the nashi (Asian) variety, perhaps over a century old, are growing directly opposite the school, behind a bus stop on Mona Vale Rd.

St Ives Sydney Grammar Preparatory School 1967

St Ives Sydney Grammar Preparatory School 1967. Photo: Max Dupain / SG Archives

In Shorelife magazine, an interview with record-breaking tennis legend John Newcombe (who resides in Pymble) revealed he attended Sydney Grammar St Ives Preparatory for his primary school years.

The 79-year-old former world number one in both singles and doubles tennis, said, “When I drive along Mona Vale Rd, past Grammar Prep, I still have memories of big orange orchards, which are ovals now… The orange orchards got me the cane. Six on the bum. You were forbidden to go down to the orchards, so we always used to go there and have orange fights. You would get sprung and then you would get six [strokes of the cane]!”

Railway rumblings

Considering most of the privately-administered schools on Sydney’s North Shore are along the railway corridor from North Sydney to Hornsby, why is the Sydney Grammar St Ives Preparatory and Brigidine College, a girls’ Catholic secondary school a short distance away, located in the comparatively remote St Ives?

Especially as when they were both established in 1954, St Ives was relatively unpopulated, because it consisted mainly of the aforementioned orchards and a network of market gardeners.

This was because there was a serious proposal to construct a railway line from Gordon to Mona Vale, which would have run in close conjunction to Mona Vale Rd, passing through St Ives.

(Mona Vale Rd, cleared and bitumen-coated in the 1930s, was previously known as Pittwater Rd along the eastwards stretch to the Northern Beaches, and Stoney Creek Rd from St Ives west to Lane Cove Rd – now Pacific Highway. It was a city-bound dirt track for the horse-drawn timber wagons of the district’s first landholder, magistrate and emancipated convict, Daniel Dering Mathew.)

t Ives Sydney Grammar School's music students

St Ives Sydney Grammar School's music students, 1975. Photo: SG Archives

As 2075 magazine has previously explored, St Ives was initially identified by European settlers as a prime timber district; then, from the 1850s, after the forests were felled, fruit trees were planted in their stead.

St Ives was not connected to the Sydney electricity grid until 1914. Yet, it was not rezoned from ‘rural’ to ‘residential’ until 1959, five years after these two schools were opened, when new streets and houses populated the suburb.

In November 1911, the first formal proposal for a rail route between Gordon and the Northern Beaches was raised by the President of the Ku-Ring-Gai Shire Council, Rev Paul Clipsham, who said: “It would run through St Ives one of the most thriving fruit growing districts in the state. It would carry heavy consignments of fruit to Sydney and doubtless when communication with Broken Bay was opened up much of the fish supply of Sydney would be carried by it.”

However, it was voted down, due mainly to the sparse population and lack of infrastructure in the vicinity, and because a tramway along the same route was already in consideration.

St Ives Sydney Grammar Prep School in 1967

St Ives Sydney Grammar Preparatory School 1967. Photo: Max Dupain / SG Archives

In June 1921, the railway was seriously reconsidered, when John Estell MP, the NSW Secretary for Public Works and NSW Minister for Railways, inspected a proposed route from Gordon to Narrabeen through St Ives, and announced he’d “recommend” to his colleagues a new rail link to the coast. It didn’t eventuate.

Public pressure for a railway line to the coast increased as the St Ives population expanded over the coming decades. With the major development of infrastructure in the 1950s and the subsequent influx of settlers, residents felt confident St Ives would be linked by rail to the main North Shore Line at Gordon.

Indeed, the Department of Main Roads, in their 1957-58 Programme of Works, approved widening Mona Vale Rd to overcome constant traffic congestion.

Hence why it made good sense to establish Sydney Grammar Preparatory School on Mona Vale Rd, the proposed rail route.

History of Sydney Grammar School and High Achievers

Meanwhile, the school, initially built among the old citrus groves, expanded their playing fields as the orchardists alongside subdivided and sold their farmlands. A kindergarten was added to the infants and primary and its student intake increased to around 440 pupils, educated up to sixth grade, most of whom came from the surrounding district.

Nevertheless, despite the St Ives campus’ relative isolation, Sydney Grammar, along with its senior school in the city, distinguishes itself as a high-achieving educational establishment.

Story time for St Ives School students

Story time for St Ives School students,1960. Photo: SG Archives

For example, in the 2022 National Assessment Program – Literacy and Numeracy (NAPLAN), Sydney Grammar secondary school was in the top 10 best performing schools nationwide, and the top performing private school, a distinction it also achieved in 2020, 2019, 2018, 2017, 2016, 2015 and 2013.

Furthermore, notable alumni include three former Prime Ministers (the 1st, Edmund Barton, 20th, Billy McMahon and 29th, Malcolm Turnbull), Olympic gold medal swimmer Andrew ‘Boy’ Charlton, and bush poet and author of Waltzing Matilda, Banjo Patterson, as well as outstanding achievers in the world of science, creative arts, sports and academia.

However, the school students, and indeed the rest of the population of St Ives, are all still waiting for the arrival of that Gordon to Northern Beaches train service…

St Ives Sydney Grammar website

Sydney Grammar History archive

Sydney Grammar Photo archive

St Ives Sydney Grammar Preparatory School, 1960

St Ives Sydney Grammar Preparatory School, 1960. Photo: SG Archives


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