John M. Hobby Sr., 89, of Plymouth and Martha’s Vineyard, passed away peacefully on June 13, 2025, at the Newfield House in Plymouth. He was the beloved husband of the late Susan (Wilder) Hobby, and a loving father, grandfather, brother, and friend to so many who will miss him dearly.
Born in Stamford, Conn., and raised near Philadelphia, John graduated from Lehigh University in 1958, and later completed U.S. Army Officer Candidate School, an achievement he regarded with quiet pride. Though he didn’t serve in combat, he lived with a strong sense of duty, purpose, and integrity. John and Susan moved from Georgia to Chicago in their twenties before settling down with their family in Sherborn in 1971.
John made his mark in the printing press industry, where he built a respected career in marketing and sales. Known for his charisma, clear thinking, and talent for communicating and connecting with others, he became a leader in the field — and someone whose word and handshake truly meant something.
But John’s greatest legacy was the life he built with Susan. Jack and Susan met on a blind date, after which Jack pronounced that if he was able to have a second date with her, he was going to marry her. It was love at first sight, and their bond remained unshakable. When Susan suffered a stroke later in life, John stepped into the role of caregiver without hesitation. For more than 20 years, he helped her with daily rehab, lifting and loving her with strength, tenderness, and tireless devotion. Their relationship was a testament to loyalty, resilience, and deep love.
For more than two decades, John and Susan wintered at their home in White Cliffs in Plymouth, but it was their house on the water in Chilmark which they always felt was home. John embraced the rhythm of Island life — fishing, splitting wood, tending the fire, and watching the sun melt into the horizon. Every evening he would pause and say, “Look at that beautiful sunset,” as if it were the first one he’d ever seen.
John had many cherished friends from his years in Sherborn. He was an active member of the Dedham Country and Polo Club, where he spent afternoons golfing on the weekends, before fishing became his passion.
A lifelong outdoorsman, John loved fishing — especially early morning trips with his kids. He was a lifelong subscriber and looked forward to each Salt Water Sportsman magazine, quite possibly keeping every issue he ever received. Being on his boat with family and friends was truly his happy place.
He was also a loyal sports fan who never missed a golf match on TV, Red Sox game, Celtics tip-off, or Patriots kickoff. Snacks in hand — peanuts and pretzels –– he shared the experience with his grandchildren, who adored him.
A curious and thoughtful man, John was an avid reader of history, particularly the Civil War and World War II; he was an excellent conversationalist, and we will miss our talks with him.
His morning routine was sacred: a hot cup of coffee, the Martha’s Vineyard Gazette and the Boston Globe, a Sudoku puzzle, and his trusty graph paper, calculator, and perfectly sharpened pencils. He always had a budget, and he always had a plan.
Above all, John loved his family. He is survived by his children, John and Christine Hobby of Franklin, Roger and Kristen Hobby of Nantucket, and Jill and Jason Napior of West Tisbury. He was the proud and loving grandfather of Ryan, Matt, Maggie, Thomas, Lauren, Stella, Camden, and Leo; and great-grandpa to Brooks Hobby. He is also survived by his brother, Scott Hobby, and Scott’s wife Katherine of Atlanta, Ga.
John’s life was defined by his love of and loyalty to family, and his grit, witty humor, and kind heart. He lived fully and loved deeply. We will forever be grateful for all that he did for our family. A private family service will be held to honor his remarkable life.