In the 1880s Weir moved to rural Wilton, Connecticut after having acquired farm property, now the Weir Farm National Historic Site, through his marriage to Anna Baker in 1883. While here, he strengthened his friendship with artists Albert Pinkham Ryder and John Henry Twachtman. The art of Weir and Twachtman was especially well aligned, and the two sometimes painted and exhibited together. Both taught at the Art Students League. In 1889, the two artists exhibited and sold a large portion of their paintings at Ortgies Gallery in New York. Weir was also close friends with the still life and landscape painter Emil Carlsen who summered with Weir on his farm, before purchasing his own home in Falls Village, Connecticut. The pastoral setting of his farms often feature in his paintings. They were a healthy escape from the hustle and bustle of urban New York City. Weir loved working in the city, but it often became too much for him to bear. Branchville and Windham served as comfortable getaways. According to art historian Hollis Clayson, "Life on the street could often frustrate and aggravate, but contemplated from far off, experienced exclusively as a visual phenomenon, it could satisfy".