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Sidney Culverwell Oland was born in 1886 to George Culverwell Oland and Ella Young Bauld. He was educated at LaSalle Academy, St. Andrew's School, Annapolis Royal, St. Francis Xavier College, and the United States Brewers' Academy in New York. He married Linda deBedia in 1912, with whom he had four children: Victor, Bruce, Don, and Amadita.
In 1900, Sidney joined the 82nd Abegweit Regiment. Two years later, he transferred to the P.E.I. Light Horse mounted unit. In 1904, Sidney became Provisional Lieutenant in the 1st Halifax Regiment, Canadian Artillery and competed with the British Artillery Team in Canada and Great Britain in 1907 and 1911. During the First World War, he commanded the 6th Battery at Fort McNab on McNab's Island, Nova Scotia. In addition, as a captain in the Artillery, Sidney mobilized a section of the Canadian Field Artillery. He later served in France as Commander of the 66th Battery, C.F.A., the 144th Brigade, C.F.A., and the 1st. After the war, Sidney reorganized the Halifax Coast Regiment and assumed command.
From 1922 to 1925, Sidney travelled to explore different business possibilities. In 1922, he spent the winter in Havana, Cuba with his family. During this time, he was hired as an agent for the St. John Brewery and had their bottled beer shipped to restaurants and hotels in Cuba. He also spent some time in Holywood, California acting and directing silent films until he settled in Halifax and actively participated in his family's brewery business, Oland and Son Limited and A. Keith and Son Limited.
In 1927, Sidney purchased a house on Young Avenue in Halifax and named it "Lindola" after his wife, Linda. This house was a centre for social activity, as Linda Oland was fond of hosting events. Upon his wife's death in 1966, Sidney presented the City of Halifax with a memorial fountain located in Victoria Park, known as the "Linda Oland Memorial Fountain." He also established the Linda Oland Endowed Scholarship at Mount Saint Vincent University in memory of his deceased wife.
Sidney Oland had many interests, including sailing ships, fishing, rare stamp collecting, and gold-mining. He was an avid sailor and owner of many sailing vessels. In 1905, he purchased a sloop-yacht called "Lady Betty" and used her for local fishing trips and races. He later sailed further on his ninety-foot schooner "Nomad" and later on the seventy foot motor cruiser called "Lady Betty II".
Throughout his life, Sidney was a member of a plethora of organizations and clubs. His many memberships included: Commodore of the Royal Nova Scotia Yacht Squadron; member of New York yacht club; Halifax Club; Ashburn Golf Club; Honorary Consul General of Peru; Honorary LL.D. St. Mary's University and member of the Senate (Halifax, NS); Chairman of the Board of Governors Nova Scotia Division Corps of Commissionaires; Director of the Headquarters of Commissionaires in Montreal; founding director of the Theatre Arts Guild; and Director of the National Gallery of Ottawa.
In addition to Sidney's noteworthy memberships, he was decorated by several organizations. His honours and decorations included: Knight of the Sovereign Military Order of Malta; Commander of the Order of St. John of Jerusalem; Chevalier of the Order of Merit of Peru; Volunteer Decoration of Canada; recipient of honorary degrees from St. Francis Xavier University, St. Mary's University, and the Nova Scotia College of Art and Design; and honorary Aide-de-Camp to four Governor Generals of Canada.
As a business person, Sidney held the title of President for Oland and Son Limited and A. Keith and Son Limited. He was also the Director of the Eastern Trust Company, National life Assurance Company in Toronto, Bens Holdings Limited, Maritime Paper Products Limited, Halifax Developments Limited, Canada Permanent Trust Company, and Industrial Containers Limited.