Grass Island's Little Red Shack was built by local druggist J. Harrison Monroe in 1914 as a summer cottage for his family, who spent time there fishing, picnicking, and gathering socially. In earlier times, similar shacks lined the shoreline, though few survive today. Originally standing on the west shore of Grass Island, the shack was destroyed by an accidental fire around 1936 and was rebuilt by the family in 1940, but hurricanes and threatening tides continued to create problems. In 1950 the family moved the cottage to its present location, and in 1965 the Town of Guilford purchased the landmark and the surrounding seven acres. After decades of storms and vandalism, the shack received a full renovation in 2016 led by Eagle Scout John Markowski as part of the Save The Shack Project, an effort that drew strong community support and renewed appreciation for its historical importance. Over time, Grass Island and the Little Red Shack came to symbolize simpler times and became an iconic Guilford image in paintings and photographs, treasured by the town.