Immediate Support: 1-413-243-0204

Hockey 03


Craig Matthew Whalen

December 28, 1963 ~ September 19, 2019 (age 55)

Craig Matthew Whalen, 55 of Stockbridge, MA passed away on Thursday, September 19, 2019 at Baystate Medical Center.

Born in Great Barrington on December 28, 1963, he is the son of Raymond “Skip” and Myra Whalen. Craig was a graduate of MMRHS, Class of 1982.

Craig worked at some renown establishments including Cranwell, Blantyre, Red Lion Inn, Canyon Ranch and Ray Murray Inc. His favorite job was working as a security guard at BPAC, Springfield and Stratton, where he could hang out backstage with the likes of Carlos Santana, Kansas, Buddy Guy, John Lee Hooker, Frampton and Muddy Waters.

Craig was a passionate Boston sports fan and attended many championship parades.  His true obsession, however, was the Boston Bruins where he would often call WEEI to banter with their hosts about controversial topics.

Aside from sports, Craig loved his cars having a ‘69 Cutlass, ‘76 Camaro, but most of all his ‘86 Mercury Capris and Bultaco. He also enjoyed time spent fishing at the cottage on Greenwater Pond and preparing food to share with family and friends.

Craig is best known for his infectious smile, his big heart and his signature thumbs up. Many may know him as the self-proclaimed “Mayor of Stockbridge.”

He is survived by his father Raymond “Skip” Whalen, mother Myra, brother Keith Whalen, sister in law, Sue Whalen, niece Isabelle Whalen and nephew Brady Whalen. He is also survived by many Aunts, Uncles, Cousins and close friends.

A celebration of Craig’s life will be held on Sunday, September 29, 2019 from 1-4 at the Stockbridge Sportsmen’s Club. In lieu of flowers, memorial contributions may be made in his name to Alzheimer’s Association, American Cancer Society or Stockbridge Sportsmen’s Club in c/o the Kelly Funeral Home    3 Main Street   Lee, MA   01238.

If you would like to leave a message of condolence or share pictures with the family, please visit our web site at

Donations may be made to:

Alzheimer's Association
C/O Kelly Funeral Home 3 Main St., Lee MA 01238

This will support Team Mike in the Walk to End Alzheimers.

American Cancer Society
in c/o The Kelly Funeral Home 3 Main Street, Lee MA 01238

Stockbridge Sportsmens Club
C/O Kelly Funeral Home 3 Main St., Lee MA 01238

© 2019 Kelly Funeral Home. All Rights Reserved. Funeral Home website by CFS