Hiram grew up in the Berkshire Hills of western Massachusetts, in the town of North Adams. As many people in the 19th century followed chain migration west, Hiram followed his Massachusetts neighbors, the Carpenters, west to Warrenville in 1835. Abel and Philo Carpenter had made the initial journey to Chicago in 1832. Philo was coaxed further west by a Julius Warren, a New Yorker selling off his recently settled land in the new town of Warrenville. Abel would soon follow and start Warrenville’s first general store and marry one of Julius Warren's sisters. News of promising new ventures spread quickly back to North Adams where times were difficult for many. Hiram Leonard joined the group of Easterners heading west in the hopes of success.

As a bachelor, Hiram moved to Chicago at the age of 25 and clerked in Philo Carpenter’s drug store for a short period of time before buying land from Abel Carpenter in Warrenville and striking out on his own. Hiram’s home at 3S381 Winfield Road was finished in 1838 and he began helping cultivate the businesses of the growing town of Warrenville. Hiram was a man of all trades, cutting hair, writing deeds, repairing clocks, and grafting fruit trees. Officially he was a justice of the peace, but also worked as a broom manufacturer, merchant, druggist and post office master.

With many jobs and endeavors to pursue, Hiram was a busy, busy man. In 1859 his own store was built and opened on Big Woods Road near the river, present day 28W180 Warrenville Road. Not only did his constant work tire and stress Hiram, but he also dealt with many personal trials that no doubt added to his burden. Hiram’s sister was also mentally-ill for most of her life. Hiram took care of her and ensured that she had round-the-clock caretakers. The stress of nursing his sister is clear from his journal. She was eventually committed in the summer of 1862 and as the devoted brother, Hiram saw her to the mental institution in St. Louis.

Although Hiram was a bachelor, for many years he had helped his housekeeper, Mary Wray’s family. He raised her two children and provided all that he could for the entire family. After her death, Hiram continued to care for the family. When her son, William went off to war in 1862, Hiram employed his wife Caroline and helped her care for her son. William, like many Civil War soldiers tragically perished in the bloody battle between North and South. Hiram continued to care for Caroline and her son, William Wray, Jr. and at the age of 64 he married her, a widow just 35 years of age. When Hiram died on November 6, 1878 at the age of 68, Caroline and her family inherited his property. His home stayed in the Wray family for many years after.