Cartwright Funeral Homes


MONTGOMERY, Gary E., of Middleboro MA, formerly of Randolph, passed away unexpectedly on Thursday, November 5, 2020, at the age of 76.

Gary was born to Barbara Chute and Earl Montgomery in Boston MA August 7, 1944. He lived in Randolph MA for most of his life, where he married his longtime girlfriend, Eleanor M. Knights, on April 6, 1963. Gary was on the auxillary police force before becoming a member of the Randolph police department. Gary loved hanging with his buddies, fishing and hunting in his younger years. Later in life he was an avid record collector. He was a lifelong member of Randolph Elks Lodge #2130 and was a chaperone and driver of the equipment truck for the Randolph Amvets drum and bugle corps.

He is survived by his wife of 57 years Eleanor Montgomery, a sister Deborah Almon of Wareham and a brother Robert Montgomery of Randolph. His oldest brother Frederick Montgomery passed away in 2018. Gary had two daughters, Kathie A. Ludecker of Middleboro, and Gina E. Montgomery of Framingham. He was fortunate to have 4 grandchildren, Erin, Patrick, Katie and Lindsey and 2 grand puppies, “Cheeto” and “Macchiato”. He adored his 2 great granddaughters, Brianna and Olivia and loved to watch them after school and play computer games with them.

Gary lived his life the way he wanted. Everyone knew him as a character with a great sense of humor. He loved to spend time with his family, smoke, play cards, travel to Aruba and Las Vegas and would have loved to spend his last days at the Blackjack table at any Casino.

In the end Gary was in a rehabilitation facility recovering from Colon Cancer surgery when he had a cardiac event and passed away.

In keeping with the Covid-19 guidelines, which include face coverings, social distancing and wait times in line due to temporary limited capacity, relatives and friends are respectfully invited to attend visiting hours on Wednesday, November 11th from 4:00 – 7:00 PM in the Cartwright Funeral Home, 419 No. Main St. (RT 28), Randolph. A private Funeral Service will be held on Thursday, November 12th in the Funeral Home. Burial will follow in the Central Cemetery, Randolph. For directions or to leave a sympathy message for the family, visit

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