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REMEMBER THIS: Newmarket Old Boys gathered for 1939 reunion

History Hound Richard MacLeod recalls the time when successful men came 'home' to relive their experiences and tell stories of the past, while war loomed ahead

Let's go back in time to 1939 to the Newmarket Old Boys Reunion.

I have made mention of this event in a few columns, but I think it was so momentous that it deserves its own column.

The 1939 Newmarket Old Boys Reunion was predicated on the fact that many of the children and grandchildren of Newmarket’s pioneers had left the area to find jobs and land of their own. Their desire to see the old homestead and visit family and childhood friends was the reason behind the reunion here.

These three or four-day events were held in nearly every village, town and city, usually around the Civic Holiday (Aug. 1). The Old Boys Reunion in Newmarket took place June 29 to July 2, 1939, with “those who were born locally encouraged to return for these few days to relive their experiences and to retell the story of our past.”

The 1939 reunion, a sequel to the visit of the old boys in 1901, featured prominent former residents. The name, as it implies, referred to what was essentially a male reunion, which was in keeping with the times, but it still irked my mother and grandmother, who rightly pointed out the term "prominent citizens" must include our female citizenry. You will find stories of the many prominent citizens who were, indeed, female in my earlier columns.

The term old boys seems to have found its way into our vocabulary referencing the alumni or ex-students of private schools and universities, primarily in the United Kingdom and throughout the Commonwealth. Specific identifiers were often attached, derived from the school’s name, founder or location, such as Old Etonian or Old Oxford.

While the original old boys term was specific to males’ membership, modern use of the term now includes the gender-neutral terms ‘old boys and girls’ to be inclusive of their female membership. Today, we equate the term as taking on a more negative connotation, representing the preservation of social elites and the marginalization of women and other underrepresented groups.

As I mentioned above, the purpose of the Old Boys Reunion and, specifically, the 1939 reunion was as follows:

  • To bring together prominent former residents of Newmarket who had gone on to achieve success elsewhere.
  • To attract the “hundreds of prominent ‘old boys’” back to Newmarket and allow these influential former residents to reconnect with their hometown.
  • To strengthen the community’s sense of identity and history during a pivotal period.
  • As a diversion as Canada was preparing to enter the Second World War, allowing the town to come together and reflect on its past during this challenging historical moment.
  • To preserve and celebrate Newmarket’s history and heritage.
  • The reunion was part of a much broader Old Boys Reunion movement that aimed to reconnect communities with their pasts.
  • Provided an opportunity for former residents to share stories and memories of Newmarket’s history.
  • To generate a source of income for local businesses and an influx of capital.

The Old Boys Reunion brought together hundreds of prominent old boys who had lived in Newmarket and gone on to achieve success elsewhere.

The reunion featured long parades that circled through the town, with crowds lining the streets to cheer on the participants. Events included minstrel shows, which  were held in the town hall and were a major highlight of the festivities, as well as picnics, dances and sports.

It provided an opportunity for the entire town to come together and celebrate its history and heritage, reconnecting local families with their ancestors who had moved on in the world.

In his keynote address, Sir William Mulock reminisced at the Old Boys Reunion about the changes that had taken place during his lifetime, saying, “I am thinking of the stage era long before automobiles or trains. The moment of the arrival of the stage was a great event in those days. Every mile along Yonge Street there was a tavern, and I am told that some of the passengers were in a merry mood when they reached Newmarket.”

From the Newmarket Era of the day, we know the attendees included a virtual “who’s who of expats” and that the reunion was described as “an incredible time for all those who visited and for those locally who attended.”

Some of the prominent old boys mentioned include local government officials like the mayor, reeve, deputy reeve, and town councillors, as well as community leaders in law enforcement, education and several other fields.

So, who did the 1939 reunion feature as prominent guests? According to the souvenir booklet, some of the prominent citizens that attended included:

  • The mayor, Dr. S.J. Boyd
  • The reeve, Fred Lundy
  • The deputy reeve, Joseph Vale
  • Several town councillors, including Frank Bowser, William Dixon, Arthur Evans, Dennis Mungoven, Joel Spillette and Albert Higginson
  • The town clerk-treasurer, Norman Mathews
  • The Crown attorney, N.L. Mathews
  • The local bailiff, Peter Trivett
  • The police chief, James Sloss
  • The fire department leaders, Wesley Osbourne and W. Woodliffe 
  • The magistrate of the court, W. Woodliffe
  • The clerk of the court, Allan Mills 
  • The principal of Newmarket High School, J.B. Bastedo
  • The headmaster of Pickering College, Harry Beer
  • Sir William Mulock, Canada’s Renaissance Man
  • Ernest Charlton Bogart, prominent Toronto barrister
  • Walter C. Cain, deputy minister of lands and forests in Ontario
  • Stanley G. Brock, founder of Canada Packers

There have been numerous attempts to recreate a series of homecoming events. In 1981, a Newmarket High School reunion was held, drawing more than 6,000 people and generating “a groundswell of affection” for the old school. The Old Boys Reunion concept has evolved to focus more specifically on schools and organizational alumni over the years.

The Old Boys Reunion and later high school reunions demonstrate the enduring significance of these events to Newmarket’s history and the strong community ties they often foster. We held a Quaker weekend, where we invited ancestors of our former Quaker founders to return with a medium of success.

Celebrations centred around the centenary of our incorporation as a village and then a town were based on this concept of returning home and reconnecting with one’s roots.

In summary, the Old Boys Reunion in Newmarket in 1939-40 was a significant event that brought together many prominent former residents, reconnected the community, and shed light on the town’s rich historical importance during a pivotal moment in Canadian history.

Additional sources: Newmarket Old Boys Reunion souvenir booklet, 1939; The History of The Town of Newmarket by Ethel Trewhella; Pages - Our History - YRDSB; Old Town Hall -; (PDF) Original and microfilmed newspaper collections in the Archives of … Old Boy Network - Definition & Meaning - Merriam-Webster; The Newmarket Era, Herald, and Toronto Star

Newmarket resident Richard MacLeod, the History Hound, has been a local historian for more than 40 years. He writes a weekly feature about our town’s history in partnership with NewmarketToday, conducts heritage lectures and walking tours of local interest, and leads local oral history interviews.

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About the Author: Richard MacLeod

Newmarket resident Richard MacLeod — the History Hound — has been a local historian for more than 40 years
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