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Harold T. Flanagan

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“Hello,It has taken me a really long time to write about Harold, because he meant a lot to me and my sister.My sister and I worked at the local...Read More »
1 of 4 | Posted by: Emily Burke

“I was saddened to see Harold has passed away. When I met him, we hit it off immediately. He was a very special individual, with lots of knowledge and...Read More »
2 of 4 | Posted by: Kent and Alice Carlson

“Our deepest sympathy to the Flanagan and Winters families. As neighbors for over 40 years Sonny was a wonderful neighbor and we will miss him as...Read More »
3 of 4 | Posted by: John and Judi Kozak

“From our days at TLC thru many years of service together fond memories remain! May you rest in peace. Bob Weitzel BG Ct Ret.(boom boom) ”
4 of 4 | Posted by: Bob Weitzel


Harold T. Flanagan, 79, of Windsor, passed away Tuesday, August 5, 2014 after a long illness. He died peacefully in his home with family by his side. Born August 14, 1934, in Hartford, CT, Harold was the son of the late Harold B. and Genevieve (Crowley) Flanagan. He grew up in Hartford and graduated from Holy Trinity in 1952. He also attended the Morse School of Business. In 1952 he began a military career that spanned over 40 years, including serving in the Korean War. He started off in the U.S. Air Force and served as an Airman in the Security Forces during the Korean War where he was assigned to guard airfields. He completed his enlistment in the USAF as a Senior Airman and joined the regular Army in 1955, where he was assigned to the 10th Infantry Division based at Fort Riley, Kansas, and Aschaffenburg, Germany. Harold enlisted with the Connecticut Army National Guard in October 1960, initially serving with the 243rd Signal Battalion, followed by the 169th Infantry Regiment Battle Group and then the HHC 43rd Infantry Division Headquarters. He rose through the ranks from Specialist 4 to Command Sergeant Major, and then to Chief Warrant Officer 2 in 1979, after which he was transferred to HHC, 1st Battalion, 169th Infantry. His final assignment was at the USPFO Connecticut Army National Guard Headquarters, from 1982 until his retirement as Chief Warrant Officer 4 in December 1993. His awards include the Meritorious Service Medal; U.S. Army Commendation Medal; U.S. Army Metal of Merit; Army Good Conduct Medal; Armed Forces Achievement Medal, 5th award; Armed Forces Reserve Medal; Humanitarian Service Medal; National Defense Service Medal; Connecticut Long Service Medal for 30 years of service; and Expert Badge with Rifle Bar, Pistol Bar, and Carbine Bar. He also received many achievement awards and letters of professionalism within the Military Department, Connecticut Army National Guard. His most recent award was Honorary Captain, 1st Company of the Governor's Foot Guard, presented on June 14, 2010 by the Command of Major Commandant William Oefinger. He also received a post-retirement promotion to Chief Warrant Officer 5. Harold enjoyed many pursuits outside the military. He loved spending time with family, attending fife and drum musters around the state, tending to his garden, fishing, and watching John Wayne movies. Harold was predeceased by his wife of 43 years, Judith Pinnell Flanagan, who died August 7, 2012. He leaves five children: COL John F. Winters, currently stationed in Germany, and his wife Darla; Lynn Flanagan Bernier and her husband Rhoderick of Manchester; Mark J. Winters and his partner Sandi Foster of Loudon, N.H.; Joel E. Winters of West Cape May, N.J.; and Melanie A. Winters and her husband Robert Mosher of Whitingham, VT. He also leaves two brothers, John Flanagan and his wife Marilyn of Coventry, and William Flanagan and his wife Phyllis of Dunedin, FL, and a sister, Mary Alice Piro and her husband James of Columbia. He also leaves seven grandchildren, a great-grandchild, and many nieces, nephews and cousins. His family will receive friends on Friday, August 8 from 5–8 PM at Carmon Poquonock Funeral Home, 1816 Poquonock Ave. (Rte. 75), Poquonock section of Windsor. A mass of Christian Burial will be held Saturday, August 9 at 1 PM at St. Joseph Church, 1747 Poquonock Ave. Burial will be in St. Joseph Cemetery.