Catoonah Street in the 19th Century was a center, albeit small, of the shirt-making industry, thanks to a man named D. Smith Sholes and his partner, Edward H. Smith.

David Smith Sholes was born in Ridgefield in 1839, son of a shoemaker who’d moved here from Vermont. At 15, he became a clerk at Henry Smith’s store on Main Street but after a few years went to Bridgeport to learn bookkeeping.

He returned to Ridgefield and, with Smith, acquired the Ridgefield Shirt Factory, founded in the 1840s by George Hunt. The factory was at first located in the Big Shop, a large building that stood where the First Congregational Church is now (and was moved and is now the home of Terra Sole and Luc’s restaurants off the Bailey Avenue parking lot.) The shirt making operations later moved to Catoonah Street on the site of the current Ridgefield Fire Department headquarters.

“Colored shirts were a specialty of the factory, which employed as many as sixty persons at one time,” said historian Silvio Bedini. “The chief market was New York City.”

However, many more “employees,” mostly women but including a few men, worked from their homes. Sholes and Smith would provide them with packages of shirt “components” and the women would sew them together in their spare time. The final product was packaged at the factory. The New York Times reported in 1860 that 1,100 home-working women in the area were sewing for Ridgefield Shirt.

Probably faced with competition from large-scale, mechanized clothing operations in New York City, the factory closed around 1893.

By then Sholes had become a major community leader. He helped found the Ridgefield Savings Bank, now Fairfield County Bank, and was its president from 1903 until his death in 1907. He also helped found the First National Bank of Ridgefield in 1900. A Democrat, he was appointed postmaster in 1886 by President Grover Cleveland, also a Democrat. When Cleveland left office, so did Sholes, but when Cleveland returned for a second term, so did Sholes.

He served as a town assessor, a registrar of voters, the probate judge, treasurer of the Ridgefield Water Supply Company, and clerk of St. Stephen’s Church for a quarter of a century. He also helped found a circulating library that grew into the Ridgefield Library, of which he became treasurer.

After his death, he was remembered as a kind and helpful man, one of Ridgefield’s “sturdy citizens, whose place it seems impossible to fill … Many can testify to his kindness in hours of trouble.” —Jack Sanders