York River Yacht Haven treats 12 orphans from the Milton Hershey School
In perhaps the most significant sail of my life, I got to take out 12 orphans from the Milton Hershey School.
Broken into two 2-hour sails with six boys each, they got to learn how to sail the York River off Yorktown and to enjoy the luxury of cruising on a beautiful June day.
Their teachers and accompanists were Cathi and Phil Bertrand. Phil said, “We have them live in a house together to learn life skills, teamwork, organization, time management and so on. There are hundreds of houses like ours, because the school itself has 2,200 students in elementary through high school. Our work is supported by an endowment that Milton Hershey made years ago of $5 billion that is now worth $23 billion.”
Because of festivities at Yorktown spanning four days, they got see the Thunderbird jets scream overhead. Back on the water, they saw a US Navy hovercraft gear up and charge right toward us (seemingly). It was exciting to me, so I can only imagine what it was like for them on their first time on a boat. Coincidence meets opportunity.
York River Yacht Haven treats 12 orphans from the Milton Hershey School
The Milton Hershey School in Hershey, Pennsylvania, stands as one of the most remarkable and enduring philanthropic institutions in the United States. Founded in 1909 by chocolate magnate Milton S. Hershey and his wife, Catherine, the school was conceived not as a charitable afterthought but as the centerpiece of the Hersheys’ belief that wealth should serve a broader social purpose. Today the school continues to embody that mission, providing life‑changing educational and residential opportunities to children from low‑income backgrounds across the country.
From its earliest days, the school was designed to provide more than classroom instruction. Hershey believed deeply in the value of structure, discipline, and hands‑on learning. Students lived in small group homes, worked on the school’s farms, and learned trades that would prepare them for adulthood. Over time, the curriculum expanded beyond vocational training to include a full academic program, extracurricular activities, and college or career preparation. The school gradually opened its doors to girls in the 1970s and later broadened its mission to serve children from a wide range of family circumstances, not only orphans.
What sets Milton Hershey School apart is the scale and depth of its support. Students receive full scholarships covering housing, meals, clothing, medical and dental care, counseling, and education. The school’s campus—spanning more than 10,000 acres—is a blend of farmland, academic buildings, athletic facilities, and student homes. With an enrollment of more than 2,000 students, it is one of the largest residential schools in the world.
At its core, the Milton Hershey School is a living expression of its founder’s belief that opportunity should not be limited by circumstance. More than 100 years after its founding, the school continues to transform lives—one child at a time—through a blend of stability, education, and the simple but powerful idea that every child deserves a chance to thrive.
Thanks to York River Yacht Haven, they got to sail out of a magnificent marina into an expansive river during the 250th celebrations. Top that.
Capt. Bill O’Donovan
