Julian Alden Weir authorized the construction of Weir Pond in 1896 using prize money won from a Boston Art Club exhibition for his painting The Truants. The pond covers approximately four acres. Workers constructed an earthen dam in 1896 to from the pond. The dam extends for over 200 feet along the northeast perimeter of the pond and varies in width from eight to ten feet. A roughly circular island of land stood in the northeast section of the pond after its construction in 1896. Workers likely left this circular section unexcavated and when the pond filled with water, an island was formed. Julian Alden Weir erected a summerhouse on the center of the island. Weir's older brother John, managing the farm while Weir resided in New York, recorded the structure in a 1904 letter describing, "We often go on the pond, and over to the summerhouse for tea, and stroll about the fields which never looked more beautiful." Weir was primarily interested in using the pond for fishing. Caro Weir Ely recalled many an early morning accompanying her father for fishing expeditions. However, when the pond froze blocks would be cut and stored in the Ice House. Under these frosty conditions, Weir would find inspiration to paint and created The Ice Cutters and Rabbits by the Pond. Julian Alden Weir also had a boat dock created during this time on the northwestern end of the pond, as seen in historic photographs of him and John Singer Sargent at the pond. Sometime around 1915 a boathouse might have been built on the western section of the pond.
The pond area was frequently used during the courtship of Mahonri Young and Dorothy Weir Young in the 1920s as the site of house parties, picnics, boating, and fishing. Dorothy Weir Young would still use the pond as a source of ice until the 1940s. While Mahonri Young was not an angler like Julian Alden Weir, Mahonri still found inspiration at Weir Pond. He created two ink sketches of the pond, one being a frog another of a swimmer on the bank, and a watercolor piece showing one end of the pond.
Based on notes maintained by Dorothy Weir Young, a smaller concrete dam was constructed along the toe of the earthen dam in 1937. The Summerhouse was reduced to remnants or disappeared entirely in the 1930s. Mahonri Young and Dorothy Weir Young had plans to build a round classical temple in its place. While stone blocks were transported down to the pond, the temple was never built. The boathouse can be seen in historic photographs of the pond.
The area around Weir Pond was not part of the sale to Sperry and Doris Andrews from Bill Young and Anges Young Lay, the heirs of Mahonri Young. However, it was the possible development of this area in the 1960s that spurned on a grassroots campaign to save Weir Pond from development. The boat house was still in existence through the 1960s, but must have fallen apart soon after.
Although no buildings remain around Weir Pond, the area is still used for artistic inspiration and as a hiking destination.