O’Sickey and his wife Algesa vacationed in the summers at their second home in Deer Isle, Maine, from 1962 to 1992. O’Sickey painted en plain air (outdoors), stating, "I don’t design it beforehand or worry about atmosphere." Instead, O’Sickey let the garden be his guide, sometimes even placing his large canvases against his house while he painted. Many of O’Sickey’s paintings are dedicated to this getaway in Maine.