Wolofsky was born in Szydłowiec, Poland, into an Hasidic community. He received a traditional Jewish education until orphaned at 15. Soon after he moved to Łódź, married Sarah Bercovitch, and immigrated to Canada via England in 1900 to join his two brothers, Aaron and Srul Dovid who were already in Montreal. Upon arrival, he opened a fruit store on St. Lawrence Boulevard. After a fire in 1907, he created the Eagle Publishing Company and started Keneder Adler, Canada's first daily Yiddish newspaper. Until the 1950s, Yiddish was Montreal's third most-spoken language, after English and French. Wolofsky served as the paper's managing editor until his death. The Keneder Adler served an ideologically diverse readership. The paper's focus was on world events, but the editorial staff understood its importance to the neighbourhood so well that they listed births and deaths on the front page. If no deaths were announced in the morning edition, it was referred to as a "clean paper." The paper promoted Jewish education, the establishment of a Canadian Jewish Congress, the creation of a Jewish Community Council, and the building of what eventually became the Jewish General Hospital. The Adler attracted Jewish writers of international renown such as HebraistReuben Brainin, who served as editor from 1912 to 1915, and featured many of Canada's Yiddish writers. Wolofsky's Adler subsidized the literary and scholarly pursuits of its associates and published many of their books. Among the books published was Canada's first Yiddish book: Moshe Elimelech Levin's Kinder Ertsiyung bay Yidn, and a local edition of the Talmud, the Adler's Shas Talmud Bavli or, as it became popularly known, the Montrealer Shas. Wolofsky also wrote for the Adler. He published three Yiddish books: a travelogue titled Eyrope un Erets-Yisroel nokh dem Veltkrig, a volume of contemporary commentary on the weekly Torah portions, Fun Eybign Kval, and a book of memoirs, Mayn Lebns Rayze. In addition, Wolofsky served as publisher of the Anglo-Jewish weekly the Canadian Jewish Chronicle. He held various leadership positions in the Montreal Jewish community, including the vice presidency of both the American Union of Polish Jews and the Canadian Jewish Congress. Samuel Bronfman called him "both a recorder and maker of Canadian history." Harry and Sarah had eight children: Philip, Dan, Sophie, Max, Diana Moishe, Saul and Miriam According to family folklore, after Moishe and Saul became involved in the Communist Party, their father asked them to change their names so as not to embarrass the family.
