Henry B. Pennington, 97
WAREHAM- Henry B. Pennington, lovingly known as “Penny,” of West Wareham, Massachusetts, passed away peacefully at his home on September 26, 2025, at the age of 97.
Penny is survived by his sister Hattie Lewis (102); granddaughters Patricia Ares and Danielle Ellis-Andrews; grandson Jeffrey Young; as well as many cherished nieces, nephews, and cousins. He was predeceased by his beloved wife Doris Pennington; his daughters Sandra Young and Janice Ellis; and his siblings Cora Jones, Bernice Walker, Prince Pennington, Hixie Hardgrove, and Hazel Proctor.
Born in North Carolina, Penny lived in several cities throughout his life, including New York and Boston, before finding his forever home in West Wareham, Massachusetts. There, he built a family and a life filled with warmth, generosity, and friendship.
A man of strong family values, integrity, and tireless work ethic, Penny was a master mechanic who retired in his fifties. Even in retirement, he never stopped working - maintaining his property, repairing equipment, and helping friends and neighbors whenever they needed him. Whether in sunshine or storms, he could often be found out in his yard, cigar in mouth, tending to his land or fixing something that needed attention.
Penny had a natural gift with animals - often called an “animal whisperer.” He had an uncanny ability to connect with creatures great and small, and he adored his horses, cows, cats, and dogs. His most faithful companion in later years was his dog Chip, who rarely left his side and brought him endless comfort and happiness. He was often heard saying to Chip, “Let’s go, big boy.”
He was more than a neighbor - he was a mentor, a storyteller, and a friend to many across generations. Known for his quick wit, sharp mind, and generous heart, Penny had a way of making everyone feel at home. His life was filled with laughter, conversation, and the steady hum of everyday love.
Penny’s happiest moments were often spent sitting in his backyard watching the trees sway, sharing stories and laughs with his family and friends, scratching a lottery ticket, having a glass of Jack, and enjoying a good cigar with his best buddy, Chip, by his side. His home was always filled with warmth, kindness, and the open-door spirit that defined him.
Those who knew him will remember his handsome smile, humor, and generous heart. He is deeply loved and will forever be missed by all. Though Wareham has lost a piece of its history, Penny’s legacy lives on through the countless lives he touched with his humor, generosity, and unshakable kindness.
A celebration of life will be held at a later date in Wareham, where close family and friends will gather to share memories of a truly remarkable man. In lieu of flowers, donations may be made to your local no-kill animal shelter in Penny’s honor.
Arrangements are by Chapman Funerals & Cremations – WAREHAM. To leave a message of condolence, please visit chapmanfuneral.com
