Robert Ramsay or R.R. Sinclair was born ca. 18 October 1842, likely in Sherbrooke, Guysborough County, Nova Scotia. His grandfather, Donald Sinclair, was a merchant who emigrated to Sherbrooke from Thurso, Scotland around 1807. He took with him his two sons, Alexander and William. Alexander married Margaret Ramsay (originally from Edinburgh) in 1830 and together they had ten children, including Robert Ramsay. The family were Anglican. Alexander and his family lived in Sherbrooke before settling in Liscomb, likely in the late 1850s or early 1860s, where they operated a large, successful sawmill, producing over 500,000 board feet of lumber, laths, and staves in 1871. After Alexander Sinclair died in 1866, the mill was operated by his sons Donald Smith, Robert Ramsay, and William James as Donald Sinclair and Bros. The brothers were also involved in shipbuilding, and the James R. Lithgow (1872) and the Three Cheers (1873) were built in their yard at Liscomb. In 1873, the Liscomb sawmill was sold, and R.R. Sinclair moved to Sherbrooke where he worked as a merchant through to the first decades of the 20th century, selling groceries and general provisions. His first store was near the McDaniel's Sherbrooke Hotel on Mill St., where he also boarded, and in 1900 he built a new store located on Main or First St., just past the bridge to Goldenville and across from Anderson's grocery store. The building was demolished in 2018. R.R. Sinclair was also a dealer and exporter of lumber and farm produce. While most of his clients and customers were farmers within the St. Mary's River region, as well as townspeople from the villages of Sherbrooke and Goldenville, he also supplied local gold mining and lumbering companies with provisions, and exported lumber to Nova Scotia building firms like Chappell Bros. in Sydney, Cape Breton. Local memory recalls that "Bob," as he was known, would buy "rafts" of lumber floated down the river from Caledonia, which he then exported on the coastal steamer, S.S. Dufferin. It is likely that Sinclair owned a sawmill on the Northwest Arm Brook in Sherbrooke, as well as a large tract of land on present-day Cameron Rd., listed as the "Sinclair Property" on the 1876 A.F. Church map of Sherbrooke, and where the R. Sinclair shipyard was also located. Sinclair built at least two schooners at his St. Mary's shipyard, the William Hayes in 1874 and the Marshall S. in 1876. At some point, he purchased 124 Cameron Rd, a large Gothic Revival house that had been built for his brother, Marshall Sinclair, a merchant in Goldenville. Later, in 1896, R.R. Sinclair purchased 8149 Main St,. Sherbrooke, which he owned until his death on 19 January 1914, in Wolfville, Nova Scotia. He is buried in Bridgetown, Nova Scotia. R.R. Sinclair was also a member of the 4th Guysborough Regiment, a militia formed in response to the Fenian raids of 1866, serving in the Liscomb area. He remained a life-long bachelor.