CHESHIRE, Mass. —  

With heavy hearts, we announce the passing of Charles “Cheeso” Massaconi, a beloved father, grandfather, friend, neighbor, and proud American veteran, who passed away peacefully at the age of 103. A lifelong resident of Cheshire, he lived a life defined by hard work, service, loyalty, and love of family and community.

Born to Pietro Massaconi and Rosina Massaconi on October 9, 1922, he was raised with strong values that guided him throughout his remarkable life. He proudly served his country in the United States Army during World War II, answering the call to duty alongside his brothers with honor and courage.

Following his military service, he dedicated 40 years of loyal employment to General Electric Company, where he was respected for his dedication and strong work ethic.

He was a proud and active member of the Veterans of Foreign Wars and the American Legion for more than 70 years, as well as the Mountain Club and many other local organizations and social groups throughout his lifetime. His friendships and community ties meant the world to him.

Sports were a lifelong passion. From 1939 to 1945, he played organized baseball for the Cheshire town team as both an outfielder and catcher. While stationed in Hawaii during his Army service, he joined the Army’s baseball team and also played fast-pitch softball. After returning home from the war, he resumed playing baseball in 1946 for the Adams KOTSKAS team. From 1948 to 1953, he played semi-professional baseball for the Tyler Aces in the city league, where he was admired for his athletic ability, competitive spirit, and love of the game. For his efforts, he was inducted into the Berkshire County UNICO Baseball Hall of Fame in 2007

He also had a deep love for the outdoors and enjoyed hunting of every kind, especially rabbits, deer, and pheasant. Fishing brought him peace and happiness, and he remained an avid fan of baseball and football throughout his life.

Known for his strength, humility, and unwavering spirit, he represented a generation of resilience and sacrifice that will never be forgotten. His life was one of service — to his country, his family, his work, and his community.

Cheeso is survived by his children, Joe Massaconi and Daniel Massaconi both of Cheshire, Charles Massaconi Jr. of Adams, Dominic Massaconi of New Lebanon, NY, and Susan Massaconi of Sarasota, FL, his grandchildren, Michael Bostwick, Mitchell and Tyler Massaconi, and Hannah Collier, and his two great grandsons, Jonah Anthony Bostwick and Jonathan Charles Bostwick. He also leaves his only surviving sibling, Edna Gregory of Cheshire, and generations of family and friends who will forever cherish his wisdom, stories, humor, and unconditional love. His legacy will continue to live on in all who had the privilege to know him.

He will be deeply missed and forever remembered.

He was predeceased by his beloved wife, the former Joan Bondini, whom he married February 9, 1952. Joan passed March 8, 2017. He was also predeceased by his daughter Krystina J. Massaconi and a grandson, Matthew Massaconi, and six siblings, Peter Massaconi Sr., Michael Massaconi Sr., Rose Graziani, Marie Kucka, Emma Massaconi and Rita Sinopoli. A  special thank you goes out to all Cheeso’s caregivers including longtime caregiver Eileen Vandervoort and Hannah Folino, who stayed with Cheeso for his closing moments.

SERVICES: Calling hours at the Dery Cheshire Funeral Home will be MONDAY, May 18, 2026 from 10 am – 12 pm. A graveside service with Military Honors will follow at Cheshire Cemetery beginning at 12:30 pm.

In lieu of flowers, Cheeso’s family asks that you raise a glass of red wine in his honor and do something for a Veteran in your life.