It is commonly understood that in 1788 Pierpoint settled on 200 acres of land along Twelve Mile Creek, now part of present-day St. Catharines. The creek that traverses the lot of land was, and still is, referred to as Dick's Creek in reference to Pierpoint's nickname "Captain Dick." Richard was given a certificate for the land in 1791, but he did not obtain full ownership of it until March of 1804. In 1806 Pierpoint sold a portion of his lot and traded the rest of it for land in the neighboring township of Louth. It is not known how, but he also lost ownership of this land at a later date.
In 1794 Richard Pierpoint and 18 other free Blacks petitioned Governor Major-General Sir John Graves Simcoe for land so that they could establish a community for themselves. Although Simcoe supported Black emigration to Canada he did not support the idea of segregated communities and therefore turned down the petition for land.
Richard Pierpoint's whereabouts between 1806 and 1812 are unknown until his reappearance at the outbreak of the War of 1812. At the age of 68, Pierpoint became the driving force behind the desire to establish an all Black military company in Niagara. His request to found such a company was originally refused, but in July of 1812, an all Black military company was organized and Richard Pierpoint was enlisted as a member. The original commander of the company was a white officer named Robert Runchey, and his eventual replacement was another white officer named George Fowler. The all Black company became known as the Coloured Corps.