Farming Rural 18

Kenneth Robert O'Brien

May 11, 1948 ~ June 12, 2022 (age 74)


It is with great sadness that we announce the passing of Kenneth R. O’Brien on June 12, 2022 surrounded by his loved ones.

Kenneth was born in Great Barrington, Ma to Joseph and Alice (Flint) O’Brien. He attended school in the Sandisfield School House.   He continued to reside in Sandisfield with Chrystal O’Brien until about 12 years ago when he then went to live with his children to enjoy his retirement with his grandchildren.

He was well known in Sandisfield for his Lawn mowing and Snowplowing Business, “O’Brien and Son”. He was a longtime employee at Maxymillian Inc. of Pittsfield, Ma. He worked on many large construction projects around the Berkshires where he earned his nick name “Killer”. Kenny was a loyal and dedicated worker, no matter what project he was on you could always depend on him. After nearly 40 years of projects and hard work he then retired to go on to his next adventure of retirement. 

Even after his “retirement” he enjoyed working so much that he went to work for his son, Gary and daughter in law, Kristen, at Gary J. O’Brien Property Services in Lee where he loved working with the lawn mowing side of the business and mostly with his good buddy Pedro & Crew. He continued with this until about 4 years ago.

Kenneth loved summer Saturday shopping trips with Kristen (Mrs. Kitzel) and the twins followed by his Saturday night where he was a regular at Lebanon Valley sitting in the Orange section with his favorite friends Russ, Pedro & Donna, cheering on his son in the #57. On Sundays you could find him walking around the neighborhood pushing his grandkids in their cars chatting with anyone he saw or a new “buddy” along the way. He loved his scratch tickets, casino tips, automotive swap meets or talking about car shows with Matt & Francine.  He loved music, dancing and daily chats with his best friend, Marvin, from Sandisfield. In his younger days he enjoyed playing “setback” cards with Bob & Linda Croze, nights dancing with Evie, Joe, Margret, Russ, & Chrystal and adventures in his later years with Betty “Bop”. He loved going to Costco and tag sale adventures with his daughter Michelle and family.

Ken is survived by his son; Gary J. O’Brien, aka Garr, and his wife Kristen, aka Mrs. Kitzel;  His daughter: Michelle O’Brien Ransom, aka shell, and Robert Brockmann; his grandchildren: McKenna “Scooter” and McKenzie “My Pride” O’Brien, Colin “little man” and Victoria “Tori” “Little Nurse” Ransom; his step grandchildren: Dylan Tyer and Sierra Besanceney

A graveside service will be held on Saturday June 18th at Sandisfield Center Cemetery on Rt 57 in Sandisfield, MA at 11 AM.  A celebration of life will follow at the Tyringham Pavilion 100 Main Road Tyringham, MA at 12:30 PM.  Calling hours will be on Friday June 17th  at Kelly’s Funeral Home from 5 – 7 PM.  

Ken’s Family would like to thank Crystal Fox for her devoted loving care, and Hospice Services of Western mass for their care.  

To send flowers to the family or plant a tree in memory of Kenneth Robert O'Brien, please visit our floral store.

Memorial Tree
A Memorial Tree was planted for Kenneth

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June 17, 2022

5:00 PM to 7:00 PM
Kelly Funeral Home
3 Main St.
Lee, MA 01238

Graveside Service
June 18, 2022

11:00 AM
Sandisfield Center Cemetery
Route 57
Sandisfield, MA 01255

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