Ann Stewart Cragg

Ann died November 23, 2023 at the age of 82 in Aurora, Colorado. She is survived by her brother, Tom Stewart, children Elizabeth ( Betsy) Tripp (spouse Jeffery), James Szyszko, and Thomas Szyszko (spouse Danielle) and her granddaughter Samantha Tripp. Her parents, James and Mary Stewart predeceased her. 

Ann was born in Pennsylvania and spent most of her childhood and teenage years in the New England area with her parents and brother, Tom. She moved to Illinois to attend Monmouth College where she met a group of lifelong friends, who refer to themselves as the Kool Dames. The eight members of the Kool Dames met their freshmen year of college when they pledged Kappa Delta sorority. Their friendship continues to this day with biweekly scheduled Zoom calls. 

Ann stayed in Illinois after graduation, got married to Joe Szyszko and started a family. When it was time for her 2 older children, Betsy and Jim, to attend preschool she decided she didn’t like the options available. She became certified in early childhood education and started her own preschool, Discovery Trail Preschool. When Ann’s youngest child, Tom, came along, he simply went to preschool with her starting at only a few weeks old. After selling Discovery Trail, her love for early childhood education continued. She found a  position as a Director of Early Childhood Programming at Palatine Park District from where eventually retired Palatine Park District. 

Ann met Bob Cragg at church and they married in 1998. Ann and Bob honeymooned in Paradise Valley Montana. That began their love for Montana. The built a house in Emigrant and spent every summer there after they retired. They enjoyed the nature, outdoor activities and the friendly, Christian community in Montana. Ann moved to Colorado in 2020, to be closer family especially her “one and only grandchild ,” Sammi. 

Ann was always positive and full of life. She made friends easily and loved to travel. She was very proud of the fact that she had visited all 50 states as well as numerous countries including visiting her son Jim in China and daughter, Betsy and family, in Germany. She hosted family trips to Alaska, state 49, and Hawaii, state 50, so that she could enjoy traveling with her children, their spouses, and her granddaughter. She was always up for an adventure and even joined her son, Tom, for several days when he walked the Appalachian Trail. 

Ann’s friendly personality, positive attitude, zest for life, and love for friends and family will be greatly missed. Memorial services for Ann were held for close friends and Family on December 16th. In lieu of flowers, donations can be made to your local Alzheimer’s Support Society.