Name: Calling hours for Joseph V. Fleming
Start: 2025-01-26T10:00:00.000Z
End: 2025-01-26T12:00:00.000Z
Location: Holmes Watkins Funeral Home

Joseph Vincent Fleming, 86, of Bolton, Connecticut, passed away on January 18, 2025 after battling dementia for the past year. Joseph is survived by his wife, Sheila Fleming, son, Joseph 'Chi' Fleming, daughter(s), Ashley Cassello and Emily Cassello, and his two grandsons, Conor Fleming and Aiden Fleming. Joseph was born to Joseph and Eleanor Fleming on January 21, 1936 in Salem, Massachusetts. While in Massachusetts, Joseph completed his schooling at Salem State College and developed his passion for Boston College Football. Ultimately, Joseph earned his degree in Educational Leadership, pursuing his passion for education as a teacher first and then as an administrator. Joseph spent many of his most joyous years as the Principal for Bolton High School. Mr. Fleming, as he was fondly referred to, ran a tight ship as Principal, having only the highest expectations for his students, taking many students under his wing over the years, guiding them toward bright futures. BHS was also where Joseph found the love of his life, Sheila. Joseph loved traveling with Sheila, visiting pubs in Ireland with her, or enjoying tropical beaches with her. Joseph loved his bulldogs, the Patriots, a good historical T.V. series and a glass of Irish Whiskey every now and then. He will be looking out for his family and friends with his best bulldog by his side, Quincy. Calling Hours will be held on Sunday, January 26th, 2025 from 10am till noon with a time for Sharing Memories. To leave an online condolence please visit www.holmeswatkins.com To send flowers to the family or plant a tree in memory of Joseph, please visit our floral store.

To plant trees in memory, please visit the Sympathy Store.

Published by WFSB on Jan. 22, 2025.

Memories and Condolences
for Joseph Fleming

11 Entries

JOSEPH PATULEIA

April 8, 2025

Joe Fleming was my Seventh-Grade teacher. I have stories and stories, but nonetheless, I am 75 and a working principal to this day, because of him!

Heather

January 31, 2025

Rest easy buddy. You were quite the character. May you R.I.P.
Heather (CNA)

Marty Hainsey

January 26, 2025

Joe, Mr L. & Ron with Stanley Cup B.I.P.

Marty Hainsey

January 26, 2025

Joe with Ron on USA National Team

Marty

January 26, 2025

Marty

January 25, 2025

Marty Hainsey

January 25, 2025

From my son Ron's earliest days in Bolton's school system his teachers were always supporting his progression and effort in hockey. Starting at age (8) Ron was competing in one of the best youth triple A hockey leagues in the country, the Metropolitan Boston Hockey League. The league not only required a high skill level it also required good grades in school. Every report card was reviewed by the coaches and every year you had to try-out for the team. In both cases if you didn't make the grades or your skill was no longer competitive that was the end for that player playing in that organization. Every teacher Ron had worked with him and supported this effort. Ron's biggest supporter and fan was Joe Fleming the Principle of Bolton High School. On behalf of my family I'd like to say one last time, thank you Joe and all the teachers that helped my son achieve his dream of becoming a Stanley Cup Champion.

We will always have you in our thoughts and hope that you will continue to smile upon us all from above,

The Hainsey family,
Marty
Kerry
Ron
Katie

Love, Nancy Larson

Planted Trees

Anne Jellison

January 24, 2025

What a great guy! Joe and I worked together in Bolton. Our administrative meetings were never dull! One memory I have is when my husband and I travelled to Ireland. Joe suggested several places to visit which we did. We were not surprised to find pictures of Joe on the walls of some pubs and someone who knew him. From one of his trips to the Emerald Isle, he brought me a magnet which I still have on my refrigerator. He touched so many lives and will be missed. So grateful to have known him! Sending heartfelt sympathy to the family,
Anne Jellison

Juli Brandt '92

January 24, 2025

So very sorry for your loss. Mr Fleming was one of two Principals who I can say made a huge impact on my life. I have never forgotten him since I graduated in 92 and I never will forget him or that beautiful fellow Bostonian accent. Godspeed Mr Fleming. Those who knew you are truly blessed

Michelle Accarpio

January 22, 2025

So sorry for your loss. Our thoughts & prayers are with you & your family at this difficult time. The Accarpio Family

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