Continuing a pattern that the Bensons would follow for years, the family left Boston during the summers. The family spent summers in New Castle, New Hampshire from 1893 to 1900, where Benson made some of his first Impressionist paintings, such as "Children in the Woods" and "The Sisters." The popularity of "The Sisters", a painting of daughters Elizabeth and Sylvia, won medals in expositions throughout the United States and in Paris, was a prelude to the successes of the next 20 years, when Benson became famous for a series of paintings of his family. After New Castle, the Bensons spent their summers on North Haven Island in Penobscot Bay in Maine at Wooster Farm. Benson made Impressionist works of his family in earnest at Wooster Farm en plein air. The summer home afforded a great view of the bay and surrounding area. Near the house was an old orchard, large fields provided plenty of space for the children to play and for a garden, and the property stood beside a wooded area.