Haileybury was founded in 1889 by Charles Cobbold Farr, who named the newly founded town after the Haileybury and Imperial Service College, his former school in England. Haileybury was formally incorporated as a town in 1904. Farr encouraged settlement in the area, penning his own promotional pamphlet, entitled "The Lake Temiskamingue District", in an effort to attract new settlers to the region. Marketed to settlers as prime agricultural land, Haileybury had only a handful of residents until the arrival of the Temiskaming and Northern Ontario Railway in the early 1900s, and the subsequent discovery of large silver deposits in neighboring Cobalt in 1903. During the Cobalt Silver Rush, Haileybury became a 'bedroom community' that served the needs of the many miners and, most famously, many mine owners and managers. These mine managers and owners were responsible for the construction of the row of stately homes, nicknamed 'Millionaire's Row' that stretched along the waterfront on what is now Lakeshore Road, many of which still stand today. In 1909, the Haileybury Hockey Club played its first and only season in the NHA. The club was taken over and moved by Montreal's Club Antique-Canadien for the following season, and became the Montreal Canadiens. By 1912, Haileybury had been named the judicial seat for the Temiskaming Region, a title it retains to this day. The town of Haileybury annexed the neighbouring community of North Cobalt in 1971.