Thompson Island is an island in the Boston Harbor, about 1 mile offshore from downtown Boston, Massachusetts. The island is managed by the Thompson Island Outward Bound Education Center, a non-profit education organization. The island is open to visitors on Saturdays and Sundays from Memorial Day through Labor Day; otherwise access is by arrangement only. Thompson Island is one of the largest, most accessible and ecologically diverse islands in the Boston Harbor Islands National Recreation Area.
The island has a size of 170 acres (0.69 km2), and the highest point is a drumlin that reaches a height of 78 feet above sea level. The rest of the island comprises low rolling hills and a salt marsh. The island has a mixed vegetation, including hardwood tree stands, remnant pear and apple orchards, ornamental trees and shrubs, and salt marsh grasses. The island has open meadows, forests, marine wetlands, sumac groves, and a variety of other geological features as well. Amenities include a formal school campus complete with classrooms, dormitories, dining hall, auditoriums, gymnasium, lab space, outdoor challenge courses, and climbing towers. At low tide, a sandbar connects it to Squaw Rock on the Squantum peninsula, allowing land travel between the two.
In 1626, four years before the Puritans arrived, David Thompson established a trading post to trade with the Neponset Indians on the island that now bears his name. Thompson was a Scot who had been superintending the settlement of Sir Ferdinando Gorges and Captain John Mason near Portsmouth, New Hampshire. For the next two centuries, Thompson Island was leased to several families for farming.
In 1833, the Boston Asylum for Indigent Boys was moved to the island, and in 1835 it merged with the Boston Farm School Society to become the Boston Asylum and Farm School for Indigent Boys. Many of the students who went to school on the island lost one or both parents, or had parents who were unable to care for them. In order for a student to be enrolled in the school, the parents or guardians had to sign a form giving the school guardianship of the boys until they were 21 years old. While on the island, parents were only able to see their child once a month during visit days and for two weeks during the summer when the boys were allowed to return home. Many "distraught mothers"  changed their minds about having their boys at the school and wanted to have them withdrawn. There are several documented cases where the school returned guardianship to the parents, who were then able to have their child come back home.
In 1955 the name was changed again to Thompson Academy. Thompson Academy became a college preparatory boarding school and continued the tradition of shelter and guidance to boys from the Boston area and beyond. During some very turbulent times, the school was a model of successful community integration based on friendship and brotherhood for several hundred boys of all backgrounds each year during the late 60s and into the mid-70s. Students participated in private school sports leagues, involved themselves in meaningful community service projects in Boston, maintained educational ties with local colleges and universities and assisted with the upkeep of Thompson Island and their school. The boys and their teachers traveled back and forth between Kelly's Landing in South Boston and the Island via the boats "Pilgrim III" and its successor, "Pilgrim IV", regularly. There were two fatal boating accidents which resulted in the death of several students and faculty. The first was in 1842, where 29 individuals died. The second was in 1892, where 9 individuals died  In 1971 a fire destroyed the main school building. The school continued to operate for another four years, closing in 1975. Many Thompson Island graduates went on to study at prestigious colleges and universities in the USA and elsewhere.
In 2015, Connie Hertzberg Mayo published a historical fiction novel, The Island of Worthy Boys, set in late 19th century Boston and at the Boston Asylum and Farm School for Indigent Boys on Thompson Island. Superintendent Bradley (served 1888-1922) and his wife are prominent characters.
In the early 1990s, David Manzo of Community Providers of Adolescent Services, Inc. d/b/a COMPASS, John Verre of the McKinley Schools, Edward F. Kelley of RFK Children's Action Corp, and Peter Willauer of Thompson Island Outward Bound Education Center, created a comprehensive residential treatment program called Citybound, for adolescents with emotional and behavioral disabilities on Thompson Island.
The Willauer School, an expeditionary learning Outward Bound school operated from 1994 to 2006. The island is currently owned by the Thompson Island Outward Bound Education Center and operates Outward Bound programs that brings more than 5,000 students and 3,000 adults a year to the island. Thompson Island Outward Bound supports its mission through donations and profits from Thompson Island Conference Center (event business running corporate outings and social events) and Outward Bound Professional (adult team-building).
In 2002, the National Park Service and the Massachusetts Department of Environmental Management purchased a conservation restriction from Thompson Island Outward Bound. With the assistance of The Trust for Public Land, who helped negotiate the deal, future development was limited to only the existing school campus. It also guaranteed permanent public access to the island, completing the permanent protection of all of the Boston Harbor Islands.
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