Timothy F. Bailey

Timothy F. Bailey Sr., age 83, passed away on Saturday, August 24, 2024, in Milton, Massachusetts, surrounded by his loving family. Born in Brockton, Massachusetts on October 17, 1940, he was the son of Harold F. and Marjorie L. (Foss) Bailey. Tim was raised in Brockton until age nine when his family moved to Harwich, Massachusetts on Cape Cod. Three years later, the family moved to Sharon, Massachusetts. Tim was a member of the Sharon High School Class of 1959.

Throughout his childhood he spent all his summers at his grandparents’ home in Southborough, Massachusetts. Tim ventured there every chance he could, thrilled to spend time away from his sisters and with his beloved horse "Boxer". 

He had an interest in working on cars and spent many afternoons and weekends customizing his Cadillac LaSalles and his 1953 Cadillac Convertible. He began his formal mechanical career at Norwood Cadillac where he continued to grow his knowledge of mechanical works, building a reputation for himself. Tim managed the Walpole Shell Station for several years, before returning to Cadillac.

In September of 1961, while attending a friend’s wedding, Timothy met the love of this life, Sandra J. DeYoung. On October 20, 1963, Timothy and Sandra were married at Saint Timothy's Church, Norwood, Massachusetts. The pair made their home in East Walpole and began to raise a family. The young family would relocate to Sharon in 1979, and after the children had grown, returned to Walpole in 1990.

In May 1974, Timothy joined the International Union Operating Engineers, Local 4. During his time with the union Tim continued to master his craft, earning an unrestricted operator’s license to utilize any type of heavy machinery and the title of “Master Mechanic”. Tim collaborated with many contractors, “Big Dig”, Deer Island, Tunnel Projects, but nothing was as exciting, or special to Tim as "building Gillette Stadium". After many years of dedication to his trade, Tim welcomed his retirement in 2006.

Tim's work was important to him, teaching his children the value of a strong work ethic. He shared his love of fly fishing with the boys, teaching them how to cast a line in Rangely Lake. He spent countless hours preparing for and then taking his family on camping adventures. He celebrated their accomplishments and showered his wife with love every day. He was thrilled when his grandchildren were born, excited to earn the title of Grampy, and see the next generation grow. He never missed an event, whether it was a game or a ceremony, always there to support. The sun rose and set on his family.

Tim enjoyed a variety of hobbies and activities. He was a car enthusiast, with a love for hot rods spending many Thursday afternoons at Gillette Stadium with the “Mass Cruisers” events. As the boys grew older, they all enjoyed Marathon Canoeing. The annual “General Clinton Canoe Regatta”, 70-mile relay from Cooperstown NY to Bainbridge NY, was a family gathering every Memorial Day for many years. He also participated in the annual “Run of the Charles” every April for many years as a member of the Corporate Relay Team, “Snoopers”. 

Tim enjoyed history, and the many hours each Saturday afternoon spent with his wonderful friends at the Sharon Historical Society. 

A creature of habit, stopping into Dunkin Donuts on Old Post Road every day to bid “Good Morning” to the girls at the window. He so enjoyed their friendly greetings.

A friend wrote, “Death leaves a heartache no one can heal. Love leaves a memory no one can steal”. May Tim paddle still water all the way to heaven. He will be remembered as a shining example of how to lead a good life. He was a master of his craft and a solid Union man. Most important he was an excellent husband, a great dad, and “Gramps”. It is with great sadness that we say goodbye.

Beloved husband of Sandra J. (DeYoung) Bailey

Loving father of Timothy F. Bailey Jr., and his wife Meghan, of Walpole, Christopher D. Bailey, and his wife Mary, of Foxborough, and Jonathan D. Bailey of Walpole

Cherished grampy of Meaghan E. Mortali, and her husband Mitchell, of Walpole, Timothy A. Bailey, and his wife Alicia, of Franklin, Jonathan C. Bailey of Enfield, New Hampshire, Tyler “Jake” Bailey of Walpole, Teaghan C. Bailey of Walpole, Bridget A. Bailey of Walpole, Jacqueline M. DeMore, and her husband Matt, of Boston, Victoria R. Bailey of Taunton, Kyle C. Bailey of Foxborough, Cody D. Bailey of Marlborough, and Angus D. Bailey of Walpole

Great grandfather of Aubrey Bailey, Myles, Maxwell, and Manning Mortali

Brother of Penelope Rowland, and her husband William, of Burbank, California, Sharon Trudgeon, and her husband Lawrence, of Northridge, California, and the late Pamela Lolli and her late husband Tim

Also survived by his dear friend, “niece”, Denise A. Pruell and her huband Jim of Walpole.

Nieces, nephews and extended “California” family

Relatives and friends are kindly invited to attend Tim's Life Celebration on Thursday, August 29th, 2024, from 4:00 - 7:00 pm in the James H. Delaney & Son Funeral Home, 48 Common Street, Walpole. Interment will be private at Knollwood Memorial Park in Canton.

In lieu of flowers, memorial donations in Tim's name may be made to the Medfield Animal Shelter at 101 Old Bridge Street Medfield, MA 02052 or by visiting https://www.medfieldshelter.com/ or to the Sharon Historical Society at P.O. Box 175, Sharon, MA 02067 or by visiting https://sharonhistoricalsociety.org/