Roxbury developed from a rural Catskills settlement established between 1788 and 1800 by families from Fairfield County, Connecticut into a village whose buildings reflect that growth, with Greek Revival and Italianate houses as well as prominent religious and educational structures. In 1836, Roxbury had a post office, two churches, two taverns, two stores, a tannery, an iron foundry, a clothing works, and twenty-five dwellings. By 1869, it had approximately 100 buildings, including five general stores, wagon shops, cooperages, a harness shop, a tannery, a dress maker and millinery shop, and several taverns. The arrival of the Ulster and Delaware Railroad in 1872 brought a new period of growth, nearly doubling the hamlet in size and linking it to Kingston and New York City, which supported the local dairy industry by transporting cheese and butter and later other products to the city. By the 1880s, regular railroad service between New York City and Catskill resorts encouraged some hotel and boarding house construction, and some families with roots in Roxbury returned to establish country and summer houses. Among them were the family of Jay Gould, who was born and raised on a farm near Roxbury, left in 1853, but retained an interest in the community; after the Dutch Reform church burned in 1891, he offered to build a new stone church, and after his death his family, especially his daughter Helen Gould, oversaw its construction. Helen Gould later built the Kirkside Estate. Roxbury was also the birthplace and summer home of naturalist John Burroughs, whose friends Henry Ford, Harvey Firestone, and Thomas Edison visited him at his cabin, Woodchuck Lodge.