Helena Strong was born in Little Bay Islands, Newfoundland, in 1879. She was the daughter of James M. Strong and Anne Mursell. She received her early education in Little Bay Islands, but was sent to St. John's Methodist College for secondary schooling. Thereafter, she came to the Mount Allison Ladies' College, where she earned a Mistress of Liberal Arts (MLA) in 1902. She subsequently taught in Botswoodville, Exploits Bay, Newfoundland.
She married Richard Anderson Squires on 17 July 1905. The couple set up residence in St. John's, Newfoundland, where Richard established a law practice. The couple had seven children.
Helena was an active philanthropist and was instrumental in the founding of a teachers college and a maternity hospital, serving as president of the Grace Hospital Auxiliary for many years.
In 1909, Richard was elected to the House of Assembly. He would spend the next 23 years involved in the political life of Newfoundland, eventually becoming prime minister. Ironically, he spent part of his time in the House trying to block suffragist efforts to get women the right to vote.
In 1930, a byelection was called at Lewisporte after the sudden death of a Member of the House of Assembly (MHA). Helena Squires was elected as the Liberal candidate with 81 per cent of the vote, thus becoming the first woman elected to the Newfoundland House of Assembly. She took her position seriously and spoke up for the people she served, but her political career was short-lived. She was defeated in her bid for re-election in the 1932 general election following a significant loss in public support for the Liberal party. It would be another 40 years before a woman again sat in the Newfoundland House of Assembly.
When Newfoundland joined Confederation in 1949, Helena Squires was elected the first president of the provincial Liberal Association. She held this position until 1958. She died in Toronto, Ontario, on 21 March 1959, and is buried in the General Protestant Cemetery in St. John's, Newfoundland.