Born on August 4, 1853 in Cincinnati, Ohio, to parents who were German immigrants, Twachtman received art instruction locally in his teens. From the mid-1870s through the mid-1880s, he traveled to Europe four times, studying in Munich from 1875 to 1877 and in Paris from 1883 to 1885. During the years that he traveled back and forth to Europe, he achieved prominence in the New York art world, becoming a leading figure among a new generation of artists who had broken from the tight realism and grandiosity of the Hudson River School to develop more individualistic modes of expression. However, until 1887, Twachtman’s base remained Cincinnati, where in 1881 he married Martha Scudder, a fellow artist. Seeking to leave a city where he felt art was unappreciated, he moved east in 1888. His family soon joined him, consisting at the time of three children. (Of the artist’s seven children, five would survive to adulthood).

On February 18, 1890, after at first renting a cottage in Greenwich, Twachtman purchased three acres of land two miles north of the main section of the town, between Round Hill Road and Horseneck Brook. His property was located in Hangroot, an area of undulating hills named probably for the tangled roots of trees that hung around its great rock formations. At the time, its residents consisted of a few African American families, whose ancestors had been enslaved in the homes of colonial settlers in Greenwich. On December 1, 1891, Twachtman acquired an additional thirteen acres that encompassed the brook. During the 1890s, he was often viewed as the American artist whose work was closest to that of the French Impressionist Claude Monet. When the two were included in a four-artist exhibition in New York in 1893, a critic stated that Twachtman had “come nearer than any other New York artist to solving some of the problems of plein aire that Monet [had] set down.” The two artists also can be compared for the distinctive ways that each used Impressionist means to capture nuances in familiar landscapes rendered in series. After leaving his Greenwich home, Twachtman lived partly at the Players Club in New York City and at the Holley House, while spending his summers in Gloucester, Massachusetts, where he died on August 8, 1902, four days after his 49th birthday.

While living in Greenwich, Twachtman taught a summer art school in nearby Cos Cob, based at the Holley family’s boarding house (now known as the Bush-Holley House, an historic house museum operated by the Greenwich Historical Society). He was a founding member in 1898 of the Ten American Painters, the group of artists who broke from the Society of American Artists to hold exhibitions exclusively of their own work, in the mode of the independent exhibitions of the French Impressionists. A “painter’s painter,” Twachtman was revered by fellow artists but unsuccessful at marketing and selling his work. During his lifetime, he was viewed as a modern artist, whose work—too advanced for his own time—would only receive its due recognition in the future.