In the early nineteenth century, Lynn was a popular location for picturesque summer houses, of which High Rock Cottage, nestled on the southern face of High Rock, remains the last major surviving example. Although High Rock Cottage has lost much of its Gothic Revival trim, originally there were porches on three sides of the front of the house and vergeboard in the gable ends. Constructed of local fieldstone, the cottage was probably designed either by Alonzo Lewis, a surveyor and architect who was responsible for the first High Rock Tower, or, more likely, his student George E. Harney, who later became a New York architect.
Although severely altered and deteriorated, High Rock Cottage holds major architectural and historical significance for Lynn and the history of New England Quakers. Members of the Hutchinson family—John, Jesse, Asa, Judson, and Abby—were Quakers who used their talent as singers to promote antislavery, women's rights, temperance, and world peace, and they built High Rock Cottage. The Hutchinson Family Singers traveled throughout the country and in Great Britain but continued to maintain their Lynn property. The house, which contained twelve rooms, fourteen closets, a bathing room, and an icehouse, was rented the first summer after its completion in 1847.
Above the house on the top of High Rock, the original tower on the rock outcropping served as both a lookout and a focal point for public celebrations. It burned in 1865 and was not replaced by the present tower until 1904. John Hutchinson had donated the site to the city, which then acquired additional property for a park and hired a local architectural firm to design a new tower. Although the domed observatory has since been removed, the stone Romanesque-style tower remains otherwise intact.