Originally the 365 acre Sherwood Farm, Captain Boland bought the property in 1871 to establish a Catholic reform school for boys. A Yonkers hat factory was destroyed by fire in the early 1890’s. The Peekskill Board of trade subsidized the companies’ relocation to Peekskill at the Boland site. The Peekskill Hat Factory was incorporated in 1895 with Anthony Ehardt as president. The sales office was located at 230 Fifth Avenue in Manhattan.
A factory advertisement announced: “Men’s, Boys, Ladies, Children; soft fur hats in various grades.” The factory received a U.S. Government contract for military hats during World War I. The factory employed several hundred men and women, many from eastern European countries such as Hungary and Poland, who worked in difficult conditions at minimal wages. The pay was $1 a day for 10 hours of work. In 1912 there were 479 workers, making it one of the largest employers in the city and responsible for settling the northern portion on town. The Trolley lines were extended to the Hat Factory in 1905 to allow workers to reach the factory at minimal cost.
A workers strike began in 1921 for improved working conditions and higher pay. After two years of labor disagreements the factory relocated to Danbury Connecticut in 1923. The Hat Factory ceased to be used and fell into disrepair. Finally the Town of Cortlandt, which had acquired title to it through unpaid taxes, sold it to Edwin J. Lockwood a well known engineer of the Borden Milk company.
The abandoned factory was rebuilt, modernized and transformed into an up to date industrial establishment. In 1979 the Green family, the current owners, purchased the property. Aside from a diverse group of tenants, the Hat Factory has established a reputation for hosting art exhibitions including The Peekskill Project 2008, Collaborative Concepts at the Hat Factory, the Art Lot and For the Love of Art.