Mrs. Judith A. Bailey

With profound sadness, we announce the unexpected passing of Judith A. Bailey on Sunday, March 9, 2025, after a brief but courageous battle with liver and pancreatic cancer. Born on September 12, 1947, Judy grew up in Hinsdale, Massachusetts, and graduated from Wahconah Regional High School in Dalton, and Berkshire Community College, in Pittsfield. Judy’s life was defined by creativity and hard work. She began her career in retail at England Brothers before running a successful seamstress and upholstering business alongside her husband. Later, she transitioned into administrative work at WUPE radio and ultimately retired as an Executive Assistant from General Electric’s Plastics Division. Even after retirement, she continued lending her expertise to one of the best bosses ever—her son-in-law—at a mortgage brokerage. A lover of nature, Judy transformed her two-acre property in Windsor, where she and James moved in 1989, into a lush haven filled with flowers, fruits, and vegetables. An avid birdwatcher, she found joy in the simple beauty of the outdoors. A world-class crafter, she created greeting cards so exquisite they could have been sold in boutiques. If you were lucky enough to receive one, you experienced how much love and artistry she put into each piece. Home improvement was another passion, and she was equally as skillful with a skilsaw as she was with a sewing needle. She designed many of her daughters’ clothes when they were young and relished overseeing home projects—often enthusiastically “directing” her husband and neighbor, who (of course!) loved every minute of it. Judy had a deep love for animals, especially her cherished pets—K.C., Gizmo, Pandora, Keebler, Hooch, Turner, Mufasa, Chewbacca, Neko, Zoe, and Zeke—as well as all the neighborhood dogs. She found immense joy in traveling with her daughters and granddaughter, putting together intricate puzzles, and spending time by the ocean. And let’s not forget her deep devotion to online shopping—UPS will surely notice her absence, and there’s a good chance a confused delivery driver will still show up at her house out of habit. Judy even had a brush with fame—literally. She was featured in Norman Rockwell’s painting Happy Birthday Miss Jones, chosen because of the shirt she was wearing. If you look closely, you’ll spot her shoulder. An incredibly strong woman, Judy was a survivor—she conquered multiple myeloma and proudly celebrated almost 30 years of sobriety. She was predeceased by her beloved husband, James R. Bailey; her brother, Timothy Peters; and her Aunt Grace Perkins. She is survived by her two wonderfully entertaining sons-in-law, Michael Sharry of Bernardston, MA, and Barrett Erwin of Auburn, MA; and her cherished granddaughter, Molly, who shares her love of crafting and nature. She also leaves behind many loving siblings from both her and her late husband’s families, a large extended family of cousins, nieces, and nephews, and a treasured community of Windsor residents. A special thank-you goes to her dearest friends and neighbors, Cindy Carrigan and Warren Mayer, for their unwavering support and love. As she reunites with our father - and likely starts lovingly nagging him again - we hope they both know how grateful we are for their guidance, support, and unwavering love. We love you forever, Mommy, from your two freakin’ amazing daughters, Suizee and (her much older sister) Sharon. Funeral Notice: In keeping with Judy’s wishes, a private funeral service will be held. The family kindly asks for privacy and appreciates your understanding. In lieu of flowers, donations in Judy’s memory may be made to the Dana-Farber Cancer Institute to support cancer research and patient care. Contributions can be sent to Dana-Farber Cancer Institute, PO BOX 849168, Boston, MA 02284, or made online at Dana-Farber.org/gift.

Mrs. Judith A. Bailey

September 12, 1947 - March 9, 2025