Welcome to the memorial page for

Raymond Gregory

January 25, 1952 ~ August 26, 2017 (age 65)

Raymond Murray Gregory, Jr., 65, Dalton, MA, entered into eternal rest on Saturday, Aug. 26, 2017 at Berkshire Medical Center surrounded by his beloved partner of 40 years, Judith Whitney, and his family.


Born in Pittsfield, MA on Jan. 25, 1952, Ray was the oldest of ten children of Raymond M. Gregory, Sr. and the late Margaret M. (Murphy) Gregory. A lifelong resident of Berkshire County, Ray graduated from Pittsfield High School in 1971, along with his classmate and brother, Rob. Throughout his life, Ray and Rob were best friends and they shared many of life’s interesting moments.


Ray worked as a glazer for Berkshire Plate Glass for 16 years. He was employed as as a laborer with Morrison’s Home Improvement, and as a custodian for St. Joseph High School, the 5 Chairs Restaurant, the GEAA, and most recently the Elks Club, where he was a member, and at the Pittsfield Police Department through Manpower.


Ray had an infectious laugh and beautiful, twinkly blue eyes. He was a kid at heart. Christmas was one of his favorite times of the year. In addition to enjoying the holiday season and all it entailed, Ray loved playing Santa Claus complete with the hat, beard, red suit and boots for the annual Children’s Christmas parties at the former Hilton Hotel, and for family and friends. Another favorite holiday for Ray was July 4th. He enjoyed the parade and put on spectacular firework displays for his nieces and nephews.


Ray was naturally gifted when it came to freehand drawing. He was the ultimate Mr. Fix It man when it came to home improvement and repairs. Ray had a knack for repairing anything that was broken. He could work on a wide range of household items from small electronics to yard tools and typically had a number of these projects underway at any given time.


He enjoyed a variety of sports. In addition to managing and playing on a recreational softball team with his brothers, Ray was an umpire for many of the county’s softball leagues over the years. He was a dedicated fan of professional football and collected most of the NFL football jackets to wear during football season.


Ray carved out his niche as a singer on the Karaoke stage at the Dalton VFW. His Neil Diamond and Elvis Presley renditions were among his fan favorites. Ray had a positive outlook on life and loved his cats - Dusty, Paws, and Sassy. They meant the world to him.


Ray is survived by his partner, Judith Whitney, of Dalton, MA, five brothers, Robert T. Gregory and his wife, Georgine, of Burlington, VT, Christopher A. Gregory and his wife, Diane, of Mesa, AZ, Paul F. Gregory and his wife, Sue, of Pittsfield, MA, John Ezra Gregory of Great Falls, VA, and Matthew G. Gregory and his wife, Debbie, of Dalton, MA, and four sisters, Shawna C. Gregory of Great Falls, VA, Charlene C. Barber and her husband, Paul, of Orlando, FL, Margaret A. Gregory-Bilotta, and her husband, John, of Hinsdale, MA, and Jane M. Gregory of Pittsfield, MA. Ray also leaves many nieces, nephews, aunts, uncles, and cousins. Ray was predeceased by his mother, Margaret M. “Peg” Gregory, who passed away in April 2017


Funeral Notice. Gregory, Raymond M. Jr., 65, died Aug. 26.  Calling hours at the DEVANNY-CONDRON FUNERAL HOME will be held Thursday morning, Aug. 31, beginning at 8:30AM followed with a Liturgy of Christian Burial at 11:00AM at St. Charles Church with the Rev. Michael Wood, administrator, officiating.  Burial will follow in St. Joseph’s Cemetery. 


In lieu of flowers, if friends desire, memorial donations may be made to the BERKSHIRE HUMANE SOCIETY in care of the funeral home.


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