Of Whitby's known 257 men and women who participated in the First World War, 43 men lost their lives. When the Whitby Branch of the Great War Veterans' Association was formed in 1920, they began raising funds to erect a war memorial to honour these fallen local soldiers.

The land on which the Cenotaph stands at Dundas and Green Streets was given to the club by Ontario County Judge and once-leader of the Home Guard Theodore McGillivray. The Cenotaph was erected in 1923 with the names of local soldiers who were killed in the First World War. It also included plaques commemorating the 116th and 182nd Battalions. In 1924, the citizens of Whitby attended the Cenotaph's dedication ceremony led by Lieutenant-Governor Harry Cockshutt. It has been the site for Whitby's Remembrance Day commemorations since then.

The Cenotaph is now a shared responsibility of the Town of Whitby and the Royal Canadian Legion Branch 112, the Great War Veterans' Association of Whitby's predecessor. It has since received additions in order to honour the local men and women who were killed during the Second World War and the Korean War.