The square was first established in 1801, around Town End Field owned by Thomas Winckley, as an exclusive residential area for the town's gentry. It is now occupied mostly by insurance, legal and other business offices, although some residential developments have recently been made. The square's gardens, now an open public park, originally consisted of private plots, each owned by a resident. A statue of Sir Robert Peel stands on one side of the central gardens opposite Cross Street, erected by public subscription in 1852.
An Italian-style villa was built in 1850 on the south corner of Cross Street (number 11), which was later used as a County Court office from the 1940s. It was demolished in 1969. On the opposite corner (number 10) was the Winckley Club, a gentlemen's club, and next to it, in Cross Street, the Literary and Philosophical Institution (later called Dr Shepherd's Library and Museum), both built in 1846 and both now demolished.
Winckley Street lies between Winckley Square and Preston's main street of Fishergate. Today it is home to mainly professional and religious service providers, including solicitors practices, a translation company, a Jesuit presbytery (taking up the majority of the northern buildings adjacent to St Wilfrids Church) as well as restaurants.
Winckley Square has been the home of several schools.
Preston Grammar School
Preston Grammar School dated back to the 15th century. In 1841 it moved to new premises in Cross Street next to the Philosophical Institution. In 1913 it relocated to Moor Park, and closed in 1967. It is not to be confused with the former Preston Manor County Grammar School in London.
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- Mahdi Al Tajir, billionaire, Scotland's richest man
- Frederick Banister, civil engineer, Chief Engineer of the London, Brighton and South Coast Railway 1860-1896
- Lawrence "Lawrie" Bond, designer of the Bond Minicar
- James Edgar Dandy, Keeper of Botany at Natural History Museum, London
- Sir John Eldon Gorst, Conservative MP for Chatham from 1875–92 and Cambridge University from 1892-1906
- Sir John Holmes GCVO CMG, Ambassador to France from 2001-7 and to Portugal from 1999-2001
- Sir John Lockwood, Master of Birkbeck College,1951–65; Vice-Chancellor of the University of London, 1955-1958
- Herbert Ponting, photographer, best known for his photographs of Captain Robert Scott's Terra Nova expedition and of Japan.
- Sir George Toulmin, Liberal MP for Bury from 1902–18
- Charles Wilfred Valentine, Professor of Education at the University of Birmingham from 1919–46 and President of the British Psychological Society from 1947-9
Preston High School
Preston High School for Girls once occupied 5 Winckley Square. It was superseded in 1907 by the Park School for Girls, which educated younger girls in Winckley Square and older girls in Moor Park Avenue. It closed in 1967.
Preston Catholic College
Preston Catholic College was a Jesuit school for boys, which opened in 1865 and closed in 1978, when its sixth form merged with Winckley Square Convent School and Larkhill Convent Grammar School to form Cardinal Newman College. At its peak in 1970, it occupied most of the west side of Winckley Square. Alumni include television football pundit Mark Lawrenson and head of the Royal Shakespeare Company, Gregory Doran.
Winckley Square Convent School
In 1875, the Society of the Holy Child Jesus formed a girls' convent school from the merger of its three convent schools, St. Walburge's of 1853, St Mary's of 1871 and English Martyr's of 1871. The new school was at 23 Winckley Square, the former home of Thomas Batty Addison, once the Recorder of Preston. As the school grew, it came to fill the whole block between the streets of East Cliff and Garden Street, reaching a peak of 850 pupils in 1962. In 1978 it suffered the same fate as the neighbouring Catholic College, the site closing in 1981. The buildings are now used as offices and a Paul Heathcote restaurant.
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- Garlington, J. (1995, new edition 2006), Images of England: Preston, Nonsuch Publishing, Stroud, ISBN 1-84588-307-1
- Hunt, D. (2003), The Wharncliffe Companion to Preston — An A to Z of Local History, Wharncliffe Books, Barnsley, ISBN 1-903425-79-4.
- Sartin, S. (2002), Preston in Focus, Landy Publishing, Blackpool, ISBN 1-872895-59-X
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