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Winning History

"My home place containing about one hundred and forty acres of land with the buildings thereon situated in Woburn, Lexington and Winchester…in trust to be used and appropriated for the establishment and maintenance of a home for orphan and other destitute children, either for their permanent or temporary care.”

Last Will and Testament of William Henry Winning 1898

On October 25, 1898, less than one year from the date of his will, William Henry Winning passed away. Those left to honor Winning's requests, John W. Johnson of Woburn, Daniel W. Pratt of Winchester, and Howard M. Munroe of Lexington, set about in their task as trustees without pause.


According to the Woburn News, 1900: The trustees "renovated the house to carry out the object outlined by the testator....and when completed will show from 20-25 rooms". The expansion aimed to accommodate "20 children at a time, for a stay of two weeks. 160 children will be able to secure a needed release from the foulness of the congested district". In 1901 the trustees, along with others, formed the Winning Home Corporation and purchased the property from the trustees for $1. For more than a century, and to this day, hundreds of children each year from the Greater Boston reap the rewards of Winning's generous gift.


Many long time residents of Woburn, Lexington and Winchester have fond memories of the Winning Home property as a summer camp, a place for riding horses, a picnic area or a place of enjoyment for children and adults alike. Parents delighted in reliving their own childhood memories through the eyes of their children.


Through the years the Winning property, known to many as the Winning Farm or the Winning Farm for Children, continuously expanded the scope of facilities and services. Scores of volunteers, groups and organizations, from the surrounding communities and beyond, devoted their personal time and resources towards the betterment of the property. From constructing new cabins and kitchens, building merry go rounds and petting zoos, clearing trees and earth to make room for new roads and swimming pools; the Winning property was a hive of activity throughout the better part of the 20th century and a bastion of joy for those to whom it was intended.


The turn of the new millennium brought with it a change in the manner in which the Board would manage Winning's legacy. After careful consideration, the Board determined that the most effective way to protect the financial stability of the Corporation and continue to help local children was through a sale of the land assets of Winning Home. The sale process produced cash assets for long-term investment, preserving approximately 50 acres of the farmland as permanent open space.


The proceeds from the sale allow the Corporation to remain true to the spirit and intent of our benefactor by working “for the benefit of children who are economically, socially, physically, emotionally or mentally handicapped or disadvantaged and their families.” Since its conversion from a landowner to a charitable trust, Winning Home has made grants over $4.3 million to area charitable organizations.