In Memory of





Obituary for Judith A. Callahan (Mole)

Judith A. Mole Callahan, 69, passed away July 19, 2022 at home.
She was born February 11, 1953, in Pittsfield, the daughter of the late Michael and Dorothy Mole. Judy graduated from Pittsfield High School in 1970. After she began her career at H&R Block, she decided to continue her education. She attended Berkshire Community College from 1993 to 1996, graduating with an associates degree. From there Judy attended the Massachusetts College of Liberal Arts from 1997 to 1999. With special approval she was allowed to graduate obtaining 2 Bachelor’s degrees at the same time: one in Business and one in Science. Through her college years she kept a 4.0 GPA.
Judy enjoyed her work at H&R Block in Pittsfield, where she was employed for 37 years. She was a Master Tax Preparer and an Enrolled Agent. Prior to that, she waitressed for many years at various upscale restaurants and inns in Lenox, MA.
Judy loved spending time with her family, especially her grandchildren. She took pride in planning and maintaining her yard with a wide variety of flowers and shrubs. Playing cards, being an avid reader and an exceptional pool player were some of her other enjoyments.
Survivors include her son, Paul A. Callahan (Kristen) of Pittsfield, and daughter, Shena L. Cachat (Michael), a brother, John M. Mole Sr. (Elaine Mole-Killion), a sister, Janice Mole Crossley, both of Pittsfield, and a brother, Michael J. Mole, Jr. (Christie) of Jacksonville, FL, along with her long-time partner William A. Ferry, and 5 grandchildren, Taylor M. Callahan, Jaxsyn J. Callahan, Reilly C. Cachat, Eric Belknap and Nicole Belknap. In addition to her family, she leaves behind her best friend from childhood, Gail Powrie of England; Taylor’s mother, Michelle Singer, who was like a second daughter to her; and her beloved Pitt Bull, Starr. Judy was also blessed with many cousins, nieces, nephews, grandnieces and grandnephews.
Judy was pre-deceased by her parents; ex-husband, James E. Callahan; brother-in-law, Bruce R. Crossley; a sister-in-law, Ceal Rath; a niece, Holly Rhodes; many cousins; and her dogs, Nash and Max.

A Liturgy of Christian Burial for Judith Callahan will be celebrated Tuesday July 26, 2022 at 11:00 AM at St. Mark's Church by the Rev. Christopher Fedoryshyn, Pastor. Burial will be private. Calling hours at FLYNN & DAGNOLI-BENCIVENGA FUNERAL HOME, 5 Elm St. Pittsfield, MA will be Monday from 4-6 PM. In lieu of flowers, memorial donations may be made to Berkshire Humane Society or the Eleanor Sonsini Shelter both of Pittsfield. To add to the Book of Memories, please visit