Winslow S. Avery

1946 - 2024

Winslow S. Avery, 77 of Pittsfield, passed away May 7, 2024 at home, with his wife Kathy and daughter Tobbie by his side. Born in Stafford Springs, CT on October 14, 1946, he was the son of the late Robert and Valerie Travis Avery.

Mr. Avery was a 1965 graduate of Stafford Springs High School, and went on to Al Prince Technical School. A United States Air Force Veteran, Mr. Avery served during the Viet Nam War. During his time in the Air Force, he completed his Jet Aircraft Mechanic, One and Two Engine Course. He was discharged in 1967 as an Air Man 3rd Class.

Winslow and his wife, the former Kathleen A. Healey, were together for 38 years.

He was a plumber for many years having worked for various companies including, B.A. Muzio Plumbing and Heating, Cheney Brothers, Inc., Mountain Craft Builders, Seven Hills Resort and Berkshire Farm Services for Youth. He then became a self-employed plumber and maintenance man. As a teenager, Winslow and his brother Robin worked in the Tabacco fields in Somers, CT. He also was a volunteer fireman in West Stafford, CT and was a past member of the Manchester, CT fire brigade. Later in his life, he worked as a teaching aid for Head Start and as a receptionist answering phones for United Cerebral Palsy. Winslow volunteered with the Boy Scouts, the Girl Scouts, the Jimmy Ride, and he was a little league coach.

Mr. Avery enjoyed gardening, playing and teaching chess, camping, hunting, playing pool on Friday afternoons with his family, and going to breakfast with friends. He was a sports fan and enjoyed watching the Green Bay Packers, LA Dodgers and LA Lakers. Winslow was also a co-captain of his high school baseball team. He was a good listener to all who needed a shoulder or some advice. He was a father figure to many younger friends.

He was a good father and grandfather to all of his children, and a loving partner to his wife Kathy.

He is survived by his wife, Kathleen Avery of Pittsfield; his 9 children, Tobbie Avery-Tracy (Lee), Doria Avery-Stevens (Nick) and Tuesday Avery, all of Vernon, CT, Scott Avery (Jenn) of Windsor, CT, Sara Avery-Oblisk (Kurtis) of Pittsfield, Katrina Avery (Dan) of Hinsdale, NH, Jareth Sykes and Jesse Sykes Jr., both of Pittsfield and Seanna Sykes (Matt) of Dalton. Thirteen grandchildren, five great-grandchildren; as well as his brother Robin Avery (Joanne) of McGraw, NY and sister, Jill Schweitzer of Stafford Springs, CT.

Besides his parents, he was predeceased by his brother, Robert W. Avery, Jr., in 2018.

Funeral services with military honors for Mr. Avery will be held, Saturday, May 18, 2024 at 3 p.m. at Dery Funeral Home, 54 Bradford St., Pittsfield. Calling hours will precede the service from 1 to 3 p.m. In lieu of flowers, memorial donations may be made in his name to Friends of Renal Dialysis in care of Dery Funeral Home.