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Sherry Downes arrived at Milton in 1955 and immediately felt at home. With the last polio epidemic raging in Boston, she and her fellow boarders were required to stay on campus. It was that time at Hathaway House where she made long-lasting relationships. “We were all remarkably alike,” she says. “We hit it off immediately, sharing inside jokes and common interests.”

Although the Girls’ School was completely separate from the Boys’ School, Sherry remembers crossing Centre Street for special events. It was at a theater production in March of 1958 that she met a boy, going home that night to write in her diary that he gave her a “nice, warm feeling.” That boy was James Bland, who would become her husband and the father of our current headmaster.

Sadly, James passed away at a young age in 1974. Sherry knew he had Milton Academy in his will, and decided to add the school to her will as well. “I was in my 30s when I added Milton to my plans,” she recalls. “You have to start somewhere. Because we benefited from those who had given before us, we had the advantage of an education worth much more than our parents paid, and the next generations deserve the same.”

Sherry’s gift is not only a tribute to her time at Milton—experiencing an exceptional education that prepared her not only for college but for life—but is also a way of looking forward. “Todd and his wife Nancy have done an amazing job of creating a community at Milton,” she says. “The community and diversity that has been built under his leadership is something that will last.”

She also has great confidence in the current and future students of Milton, including her grandchildren Nicholas, Emily, and Mary. “These kids are the future,” she says, “They want to save the world—and I think they can!”


Sherry is right. Our students are bright and headstrong, the leaders of the future. And your forethought and generosity can help them achieve new heights. Consider including Milton Academy in your will or trust, or as a beneficiary of an IRA, 401(k), or other retirement asset. To explore your options or share your intentions, please visit or contact our Office of Development at any time.

James Barrett
Director of Planned Giving