Jonathan 'Jon' Flagg

Jonathan G. Flagg, 73, a lifelong resident of Rindge, passed away on Monday, January 26, 2026, in the comfort of his home with his family by his side after a courageous battle with Pancreatic cancer.

‘Jon’ was born in Winchendon, MA on September 6, 1952, a son of the late Sydney R. and Dorothy A. (Gates) Flagg. He was educated locally and graduated with the Class of 1972 from Conant High School in Jaffrey.

Jon’s roots have always been in Rindge, he worked for the Town’s Highway Department as an Equipment Operator for 3 years before taking that experience with him to the State of NH DOT. Through his 35 years there, Jon rose through the ranks with the State, from working as a laborer, a grader operator, truck driver, assistant patrolman, and finally retiring as patrolman in 2008. While working locally, he was also able to fulfill his desire to help neighbors in need by volunteering with the Rindge Fire Department and the Meadowood County Area Fire Department in Fitzwilliam. He had served as a Forest Fire Warden for 25 years and had served as Deputy Chief and Interim Chief for the Town of Rindge, from 1998 to 2000.

In 1991, he started Jon’s Tractor Service, while also helping his friend George Peck with his construction business. Jon continued his own business doing landscaping, gardening, excavation, trucking material, mowing fields, and rototilling gardens in the area right up until his illness prevented him from working.

He always enjoyed his Mack Trucks and heavy construction equipment, and after his retirement was able to continue plowing and salting the roads as a hired contractor for NH DOT. People who knew Jon recognized when his excitement was growing just before a big Nor’easter was forecast to arrive. During his ‘retirement’, Jon had also served as the Road Agent for the Town of Sharon from 2011 to 2016

If you asked Jon, he would always say his greatest accomplishments were his loving family and Jon’s Tractor Service. He was a dedicated husband, father and grandfather.

He leaves behind his beloved wife of 47 years, Diane L. Flagg of Rindge, his two daughters, Kathy L. Flagg and Linda M. Flagg, both of Rindge, his sister, Susan Frederickson Collis of Bradenton, FL, one grandchild, a niece, a nephew, and many cousins and close friends, as well as his beloved cat Jack.

Family and friends are warmly invited to Calling Hours on Friday, January 30, 2026, from 2:00PM to 4:00PM at the Cournoyer Funeral Home, 33 River Street, Jaffrey, NH 03452.

A Fire Department Walkthrough will take place on Saturday, January 31, 2026, beginning at 1:30PM in the Rindge Congregational Church, 6 Payson Hill Road, Rindge, NH 03461. Jon’s Funeral Service will take place in the church immediately following the walkthrough.

In lieu of flowers, and because of the winter conditions, please consider making a memorial contribution in Jon’s name to either the Jaffrey-Rindge Memorial Ambulance, PO Box 107, Jaffrey, NH 03452, or to the Pancreatic Cancer Action Network, Inc. Donation Processing Center, PO Box 5041, Boone, IA 50950-0041