Middle schools students from Breakwater School in Portland met at Space gallery as part of a collaborative project based on the exhibition, “Beautiful Possibilities” by Alison Pebworth. “Beautiful Possibilities” is a traveling exhibition that engages viewers to consider what it means to be an American in the United States. Using classic Americana images and paint on canvas, Pebworth created banners that explores ideas of 19th century expansionism and the people and landscapes influenced by this westward movement. After viewing the exhibition at Space Gallery, Breakwater middle school students researched their own personal histories and incorporated their findings into individual self-portraits using a combination of drawing and wintergreen-transfer process to create a final image that gave the illusion of an old-time photograph. The final product, titled “Portrait Possibilities” was displayed at Breakwater School as part of the culminating experience.