South Boston’s Harry McDonough Sailing Center Being Added to Boston’s Irish Heritage Trail 

(October 9, 2025) – Boston Irish Tourism Association announced today that the Harry McDonough Sailing Center at Castle Island in South Boston is being added to Boston’s Irish Heritage Trail this year in tribute to the Sailing Center’s beloved founder.  

The non-profit sailing center, which provides inner-city youth with a safe, fun and accessible environment, was named to honor Harry McDonough, a proud South Boston native who taught generations of children the principles and joys of sailing for nearly three decades. The program runs each summer in July and August.

Photos by Colette Quinlin

Senator Nick Collins, who represents South Boston in the First Suffolk District, said,  “The Harry McDonough Sailing Center personifies South Boston’s finest traditions of compassion, generosity and community spirit.  Harry’s  indomitable, can-do personality shines through in the excellent work of the Sailing Center.”

McDonough, who took his first sail from the South Boston Yacht Club at age 5 with his father, John D. McDonough, was an expert sailor himself. In the 1940s, he won national sailing titles in three classes – Snipes, Indians and 210s.  

“Over the years, the Center has been a magical place for thousands of children from across greater Boston, ages 8 to 14, who get to enjoy their summers in a beautiful outdoor setting while learning positive life skills through sailing,” said Denise Cohen, a member of the Board of Directors of the Harry McDonough Sailing Center. “We have Harry to thank for that.”

McDonough graduated from South Boston High School in 1940, where he received All-Scholastic honors as a sprinter in track and a halfback in football, according to The Boston Globe.  After  enlisting in the U.S. Navy during  World War II, McDonough’s landing craft was “torpedoed by a German submarine off Italy, and he was one of a few survivors,”  the Globe wrote. 

Michael Quinlin, who created Boston’s Irish Heritage Trail in 1994, said that “the Harry McDonough Sailing Center aligns with other local landmarks that chronicle the positive role of the Boston Irish in the city’s civic, sporting and cultural life.  We are proud to add the Sailing Center to the South Boston section of the Irish Heritage Trail.”

Local sportswriter Bob Monaghan wrote that “McDonough was a fearless, fun-loving Irish Catholic with a deep compassion for those who had less than he did.” 

While McDonough’s generosity for South Boston was pervasive, his largesse went beyond the neighborhood too. In the 1980s McDonough joined his South Boston friend Billy Higgins in sending clothing and sports equipment to the Southill Children’s Fund in inner city Limerick, Ireland.  In partnership with the Carroll Center for the Blind, McDonough established the nation’s first sailing program for visually impaired children. And in 1985, he helped to bring the prestigious Courageous Sailboat, winner of The America’s Cup, to the Charlestown Navy Yard, where it is the centerpiece for a youth sailing program in Charlestown.  

McDonough died on October 9, 1990 at age 69, leaving his wife Dorothea and four children, along with countless family, friends and admirers.  His spirit will always live on at the Harry McDonough Sailing Center.

***

Formed in 1994, the Boston Irish Heritage Trail explores the city’s illustrious Irish experience, covering 300+ years of Boston’s  history, from colonial times to the present. 

In March, 2025, Boston Irish Tourism Association announced it is expanding the project by adding  new landmarks  in addition to the  20 stops in downtown Boston and 20 Boston neighborhood sites currently on the Trail.

In addition to the Harry McDonough Sailing Center, other recent additions to the Irish Heritage Trail in Massachusetts include the famous Swan Boats in the Public Garden, launched in 1877 by Irish immigrants Robert and Julia Paget; the Kip Tiernan memorial in Back Bay; the Deer Island Irish Famine Memorial in Boston Harbor, the John F. Kennedy Museum in Hyannis, Cape Cod, the Irish Round Tower in Milford and the Tom Brady Statue at Gillette Stadium in Foxborough.