Mrs. Doloris "Dee" Caldwell

Mrs. Doloris “Dee” Caldwell, 94, of Pittsfield, passed away peacefully at her home on Saturday, July 25, 2026, surrounded by those she loved so deeply, Born in Weirton, WV, on February 10, 1932, she was the daughter of the late Joseph and Audrey Dulaney Ewaskey, and was the first high school graduate in the Ewaskey family. Though Dee did not attend college, she did take night school classes for computers and cake decoration, just some of the many skills that led her to earn (in the eyes of her children) the Outstanding Mother of the Year award for nearly 73 years. Her cooking, adventuring, educational opportunities provided, firsthand experiences living history, and, of utmost importance, quality family time, shaped her into the person that her children came to look up to, respect, and love wholeheartedly. Dee passed many of her skills and her warmhearted personality to her children and grandchildren, and all the others in the neighborhood that she always welcomed with open arms! For the majority of her career, Dee worked as a sales rep for England Brothers, but was certainly not limited to solely that. She taught various classes at the Pittsfield Girls Club, girl scout and boy scout skills, as well as for the campfire girls and Sunday School. Dee was awarded the National Ski Patrol Angel Award in 1973 for outstanding contribution to Brodie Mountain Ski Patrol, and also went on to become the mother of 4 patrollers, as well as the grandmother of 4 patrollers. Additionally, Dee won multiple ceramic awards and was an active bridge player at the senior center. In any spare time that Dee did manage to find, she loved cooking, sewing, gardening, canning, quilting, and crafting. She took many cross-country trips with her family, roughing it in an old army tent, cooking over an open fire, and visiting multiple National Parks. When her children were grown, she and her husband Charlie would enjoy regular vacations to Wyoming to hunt prairie dogs or to see the Albuquerque Hot Air Balloon Festival. Doloris was predeceased by her high school sweetheart and beloved husband of 68 years, Charles “Charlie” Caldwell, who passed away in 2019. She was also predeceased by her son, Roger Caldwell, who passed in 2009, and her son-in-law James Gibbons (Laurie) in 2007. She leaves behind her children, Audrey Cullen (Thomas), Linda Clifford (Daniel), Dennis Caldwell, and Laurie Little (Timothy), as well as 7 grandchildren and three great grandchildren, all of whom she adored. Funeral Notice: Funeral services for Doloris will be Friday, July 31, 2026, at 1pm at the Dwyer Funeral Home, 776 North Street, Pittsfield MA 01201. Burial will follow at Pittsfield Cemetery. There will be an hour of visitation at the funeral home directly prior to the service, from 12pm to 1pm. In lieu of flowers, donations in her memory can be made to Elder Services of Pittsfield or the charity of your choice in care of the Dwyer Funeral Home.

Mrs. Doloris "Dee" Caldwell

February 10, 1932 - July 25, 2026