James T. Collingwood, Jr.

James T. Collingwood, Jr., 63, passed away unexpectedly at home with his wife Theresa on Monday, June 27, 2022.

He was born on December 9, 1958 in Sharon, Connecticut, the son of the late James Collingwood Sr. and Betty Markham Collingwood.

Jim was a graduate of Mount Everett Regional High School class of 1976. He also attended Alfred State University. After continuing his education, he returned to work with his parents in the family trucking business, Collingwood Transport in Sheffield Ma. Jim married the love of his life Theresa Scapin on August 25, 1979 at St Mary’s Church in Lee, Ma. Permanently settling in Ashley Falls in 1986.

After more than 20 years working for the family business, Jim started his own trucking company, JTC & Sons, a successful Rolloff and Refuse business for 15 years before merging with Daley & Sons in Lee, MA. In April of 2021 Jim was appointed Highway Superintendent for the Town of Sheffield, a job that he took great pride in.

Jim was an active member of the Sheffield Kiwanis for over 25 years, serving as president for several terms. He was also named the 2002 Kiwanian of the year. Jim played a significant role in developing the Kiwanis Scholarship Fund through their annual truck raffle, and was the number one ticket seller for 22 years.

He enjoyed his weekend trips to camp in Arlington, VT up until his death. His hobbies included golfing, bowling and hunting. He was a devoted family man, a trusted friend, and a beloved member of his community. Jim was a kind and gentle soul loved by all.

Jim is survived by his loving wife of 43 years, Theresa, his son James III (Hilary) and his son Matthew (Joelle), his three grandchildren; Madeline, Isaac and Adalie who were the joys of his life, his best friend Dave Smith, his cousin “Charlie” Julie Hannum, his two brothers Jeffrey and Bruce and too many friends, family, and extended family to list. He also leaves his loving dog Morgan, and adopted dog Cookie.

SERVICE - A service celebrating Jim’s life will be held on Wednesday, July 6 ^th at 11:00 a.m. at Finnerty & Stevens Funeral Home, 426 Main Street, Great Barrington, MA 01230, conducted by Rev. Jill Graham. Burial will follow at Sheffield Center Cemetery in Sheffield.

The family will receive friends on Tuesday, July 5 ^th from 4-7 PM at the funeral home in Great Barrington.

In lieu of flowers donations in his memory may be made to the James T. Collingwood, Jr. Memorial Family Fund c/o Finnerty & Stevens Funeral Home, 426 Main Street, Great Barrington, MA 01230.  To send remembrances to his family please go to www.finnertyandstevens.com