In Loving Memory of Charles Anderson Orcutt, III (“Charlie”)
November 17, 1935 – June 11, 2026
WESTFIELD – Charles Anderson Orcutt, III, known to nearly everyone as “Charlie,” passed away peacefully on June 11th, 2026, leaving behind a lifetime of memories, laughter, stories, and friendships.
For more than 90 years, Charlie lived a life filled with hard work, adventure, laughter, and an unwavering love for family and friends. Whether you knew him for decades or met him only once, chances are you remember his smile, his laugh, and how easy he was to talk to. He never met a stranger. In fact, many affectionately referred to him as the unofficial “Mayor of Southwick” because wherever he went, he knew someone—or quickly made a new friend.
Born on November 17th, 1935, Charlie learned the value of hard work at an early age while working on a neighbor’s farm. Those lessons stayed with him throughout his life and helped shape a man who was dependable, resilient, and always willing to lend a helping hand.
For much of his life, Charlie earned his living as a truck driver and owner-operator, logging millions of miles across the country. The open road suited him well. He loved driving, seeing new places, and sharing stories from his travels. Trucking was not simply a job—it was part of who he was. Even after retiring, he remained connected to the profession he loved, spending many hours watching Ice Road Truckers and comparing their adventures to his own experiences behind the wheel.
Long before he drove eighteen-wheelers, Charlie found excitement on two wheels. As a young man, he raced motorcycles and carried his passion for riding throughout his life. He was especially proud of his Harley-Davidson and continued riding into his late 80s, proving that age was never going to define his sense of adventure. He also loved auto racing and could always be counted on to enjoy a race and a conversation about engines, speed, and life on the road.
Charlie loved the outdoors and rarely passed up an opportunity to enjoy it. Whether camping with family, spending time on his boat, riding his Harley, or simply enjoying a great day with friends, he appreciated life’s simple pleasures. He was happiest when he was moving, exploring, helping with a project, or sharing a story.
He was also known for his playful spirit and sense of humor. His mischievous grin often hinted that he was up to something, and his laughter, often accompanied by that grin, reflected his playful spirit and love of having fun. His ability to brighten a room was one of his greatest gifts.
His first wife, Patricia, and his second wife, Constance, preceded Charlie in death as well as son-in-law Arthur Dickinson and four great-grandchildren.
He leaves behind his six daughters: Sheila Dickinson, Cynthia Trask (Doug), Linda Orcutt, Sandra Foster (Michael), Charlene Kareta (Dave), and Susan Fernandaz (Clay). He leaves behind his brother, David Orcutt (Val), and his sister, Nancy Manchino (Bob), as well as Constance’s children and their families.
His legacy continues through more than 60 nieces, nephews, grandchildren, great-grandchildren, great-great-grandchildren, and extended family members. He also leaves behind an extraordinary number of friends, including longtime friend Donny Sausville, who remained a connection to his trucking days and many other shared interests and laughs.
Those who knew Charlie will remember a man with a smile that came easily, a playful laugh, and a story always ready to share. He was hardworking but never too busy for a conversation, adventurous, and known for making people happy wherever he went. The roads he traveled stretched for millions of miles, but the impact he made on those who loved him reached even farther. His family takes comfort in knowing that his stories, values, laughter, and love will continue to live on through the generations that follow.
Charlie will be deeply missed, lovingly remembered, and forever carried in the hearts of all who knew him.
Family and friends are invited to gather for a period of visitation on Friday, June 19th, 2026, from 11:00 a.m.–12:30 p.m. at Westfield-Avalon Funeral Home, 4 Princeton Street, Westfield, MA 01085. A prayer and remembrance service will be held at 12:30 p.m. at the funeral home. Burial will be private.
To express condolences, or to share photos or memories, please visit Charlie’s memorial page at www.westfieldfuneralhome.com
