Owen Connolly was born in 1820 in Donagh, County Monaghan, Ireland. He immigrated to Prince Edward Island in 1839 and was employed on the farm of a Mr. Smallwood in Lot 28 where he remained for two years before buying a farm on the Monaghan Road. In the early 1840's, Connolly married Anne Hughes, also native of Ireland.

After his marriage, Connolly opened a store for country trade. In 1852, he moved to Charlottetown where he opened a liquor and grocery store on Dorchester Street. In 1864, Connolly built a new store on the corner of Dorchester and Queen. He later established businesses in Souris, Cardigan, and Montague. In the summer of 1870, Connolly entered into partnership with Patrick Kelly and Joseph Doyle to form Owen Connolly & Co. This partnership lasted until 1881.

Owen Connolly was a prominent member of Charlottetown society. He was the first agent on the Island for the Merchant's Bank of Halifax and when the Union Bank of Prince Edward Island (later the Merchant's Bank of PEI) was established in 1860, Connolly was appointed director and eventually, Chairman of the Board. He served as a Justice of the Peace and played an active role in exhibitions and other public occasions in Charlottetown. Also, Connolly distributed coal and blankets to the deserving poor during the winter. He died on 27 December 1887 at the age of 67.

At the time of his death, Owen Connolly owned buildings in Charlottetown, Souris, Montague Bridge, Cardigan, and Summerside as well as farms in Charlottetown Royalty, St. Peter's, Morell, and Lot 48. His large estate was administered by three appointed Trustees: Lieutenant Governor A. A. MacDonald, Chief Justice W. W. Sullivan, and future Premier Fred Peters. In his will, Owen Connolly established a bursary fund for the education of deserving Irish Catholic males. The first of the Owen Connolly Bursaries were granted to five students in 1881.

The original trustees of the Connolly served together until 13 December 1897 when Peters moved to Vancouver, British Columbia. In 1912, MacDonald died, leaving Sullivan to administer alone. The original trustees were not replaced until 27 October 1913. A petition was presented to the Provincial Legislative Assembly and an Act to Incorporate the trustees and increase the number was introduced to the House in Session in 1918 by Sir Charles Dalton, MLA. The Act was passed after a short debate. In 1968, due to the increasing costs connected to maintaining the various properties of the Connolly Estate, the real estate was disposed of and the proceeds invested in accordance with the Trustees Act. The Connolly Estate was still in existence in 2000.