Indian trader, businessman, land speculator, and politician, Samuel Street (referred to as Senior to distinguish him from his nephew) was born in 1753 in Wilton, Connecticut. In his early twenties, he traded with the Indians on the Susquehanna River. In 1778, as a Loyalist, he moved to Fort Niagara to become a merchant, provisioning the British and their Indian allies at Fort Niagara in competition with Robert Hamilton and Richard Cartwright. Unlike Hamilton, Street never developed close ties with the garrison at Fort Niagara and never formed a close relationship with a Montreal trader, and at the end of the war had to revert back to trading with the Indians and Indian Department. In 1785, he formed a partnership with John Butler's son, Andrew to build a store in Fort Niagara, importing goods. They also built a sawmill on Fifteen Mile Creek. Later he went into land speculation without any conspicuous success. He did manage to obtain a grant of 1200 acres in Willoughby Township by 1796 and later extended that by another 3600 acres. By his death in 1815, he had sold most of his land and only retained Grove Farm in Willoughby.

In 1796, he was appointed a justice of the peace, a position he held until his death. He was elected to the Upper Canada Parliament in 1796 and was elected Speaker in 1800. He did not hold the position long because he was defeated in the election that year. Returning to Parliament in 1808, he again became Speaker. About 59 years old when the War of 1812 started, he was not active in the war, serving as acting deputy paymaster of the militia.

Samuel Street Junior was a smarter businessman than his uncle and became one of the wealthiest men in Upper Canada. He was the son of Samuel Street Sr.'s brother Nehemiah and was born in 1775 in Farmington, Connecticut. He came to live with his uncle in 1787 at Chippawa after Nehemiah had been murdered in Cold Springs, New York. As a Loyalist, he was entitled to 200 acres but his uncle managed to get this increased to 600 acres.

He started working in his uncle's business at Niagara but was on his own by 1797. The next year, he formed a partnership with Thomas Clark but this ended a year later. By 1803, he was a clerk at the Bridgewater Mills on the Niagara River, just north of Chippawa. In 1807, he bought the Falls Mills from Thomas Clark, and by 1808 he was doing so well that he talked Clark into re-forming their partnership. This was to become one of Upper Canada's biggest businesses. The partners bought the Bridgewater Mills from James Durand in 1810 and so controlled both milling complexes on the Niagara River. Both were burned by the Americans in the War of 1812 but only the Falls Mills were rebuilt. With the money made from milling, Clark and Street went into moneylending. Eventually most of the businessmen in the Niagara Peninsula, such as Hamilton Merritt and James Crooks, owed them money. This led them into land and stock speculation at which they were very successful. Unlike his partner Clark, Street kept well away from direct participation in politics, preferring to keep his focus on business. When he died at Port Robinson on the Welland Canal in 1844, he left his fortune to his son, Thomas Clark Street, and his four daughters. Samuel Street Jr., his wife, and son Thomas Clark Street are buried in the Drummond Hill cemetery.