James Chaffee Loomis (1807–1877) After graduating from Yale, James Chaffee Loomis received his law training in Virginia and Connecticut. He settled in Bridgeport, Connecticut, and had a long career as a lawyer and in public service. James was elected mayor of Bridgeport, state senator, and member of the state legislature. He made two unsuccessful bids for governor of Connecticut during the Civil War, and as president of the Bridgeport Board of Education was credited with writing a blueprint for the city’s public school system. James also served as president of a number of community and professional boards and the City National Bank in Bridgeport.
Hezekiah Bradley Loomis (1809–1878) Of all the siblings, Hezekiah Bradley Loomis followed most directly in his father’s footsteps. He worked in the Loomis village store and then took up a position with his uncle and namesake, Hartford merchant Hezekiah Bradley Chaffee. He later moved to New York City and established a merchant and banking career at the Cumberland Coal Company of New York City. H.B. Loomis spent the final year of his life at the Windsor home of his sister, Abby Hayden. He was infirm and ill but was said to have been at peace to be back in his beloved hometown.
Osbert Burr Loomis (1813–1886) With the spirit of an adventurer and the eye of an artist, Osbert made his career in Charleston, South Carolina; Havana, Cuba; and New York City. He painted landscapes, still lifes, and chapel and church altar pieces but most probably earned his living as a portrait painter. A graduate of Yale, he trained with artist and inventor Samuel F.B. Morse in 1835 and traveled to Europe in 1871–72 to see the great works of art and architecture. Events of the Civil War encouraged him to leave Cuba in 1862, and he lived the remainder of his years in New York City, deeply invested and engaged in the future success of the Loomis Institute.
Abigail Sarah Loomis Hayden (1815–1898) Abby Sarah Loomis married fellow Windsor native H. Sidney Hayden in 1848 and joined him in Charleston, South Carolina, where he worked as a silver goods merchant with his brothers. Upon their return to Windsor in 1856, the couple built a striking Italianate-style home on the south side of the Broad Street Green. Abby was a devoted citizen of her hometown and was especially active in Grace Episcopal Church. She adopted and raised Sarah Elizabeth Hayden, H. Sidney’s niece, perhaps after the 1860 death of Sarah’s mother or when Sarah's father left Windsor in 1862 to fight with the Union Army.
Most intrepid among the siblings, John Mason Loomis joined the crew of a merchant vessel, traveling to India and China on the East India trade routes while he was still a teenager. In 1846, he took a clerk’s job in a Wisconsin lumber business. Two years later, he bought the company, beginning a career that spanned five decades and three states. John raised the 26th Illinois Volunteer Infantry in 1861, became its colonel, and led the regiment in 57 skirmishes. His life after the Civil War was devoted to rebuilding his once successful Chicago-based business; he accomplished this with the great acumen that he also brought to community and veterans’ associations. John helped to administer relief funds to victims of the 1871 Great Fire of Chicago and financially revived the Illinois National Guard.