Gary Wallis Caldwell of Nottingham, Maryland passed away peacefully at home in the early hours of September 12, 2026. A man of great honor yet humble demeanor, Gary was a devoted husband, father, grandfather, friend and educator, whose greatest joy came from the people he loved and the lives he touched throughout his remarkable 82 years. Always quick with a joke or some witty repartee, Gary could easily entertain an individual or a crowd with his easy and fun storytelling. He wove this talent, along with his teaching skills, into a wonderful educational career that lasted for close to 50 years.

Born in Baltimore, MD on February 28, 1944, Gary's parents were always happy that he did not turn out to be a leap year baby. He was the proud son of Vernon Rutledge Caldwell and Edna (Kidwell) Leicht. Growing up in the Highlandtown and Bowley's Quarters areas of Baltimore, he loved baseball, the Baltimore Orioles, the Baltimore Colts, "living on the Bay," being with friends, his cousins, and his mom and dad. He attended Kenwood High School, and upon graduation in 1962, Gary spent a short time in the Air Force, then returned home to work at Mars Supermarket, Korvette's, and Hutzler's Department Store in order to earn money to start college. Gary discovered his love of teaching during his years at Towson State University, from which he graduated in 1970.

Hired by Baltimore County Public Schools in February of 1970, Gary taught social studies in six different secondary schools over the course of 37 years. He met the love of his life in one of them – Cockeysville Junior High – where he and Joyce, an English teacher at the time, taught several of the same students.   Education was not simply Gary's career—it was a calling. He dedicated his entire professional life to helping young people learn, grow, and understand the world around them. For many years, he served as both social studies teacher and department chair. He was passionate about his students, his colleagues, and the opportunity to make a difference in the lives of young people. Many of his former students commented over the years about how he was able to not only make them laugh, but also inspire them to value learning as well as themselves.

Besides teaching a regular social studies schedule in BCPS, Gary also led several in-service courses, coached numerous athletic teams, sponsored many student clubs, including his favorite- student government, and mentored a myriad of student teachers. He also found time during those years to serve as an evening school teacher, a summer school teacher, a PTA president, an adult education center principal, and even an assistant funeral director at Rucks on Harford Road. This was in addition to supporting his beloved Annie and Zach in their numerous sports and activities, both after school and on weekends!

After retiring from Baltimore County Public Schools, Gary's commitment to education continued. He went on to work in the College of Education at Towson University, where he continued sharing his knowledge, experience, and love of teaching with the next generation of educators until his full retirement in 2019.

Gary loved history and had an incredible recall of significant dates and events. Fort McHenry and other historic sites around Baltimore were personal favorites of his. He loved travel, and trips to Japan (with students) and to Ireland were among his favorites. He also loved trips with friends to places like Washington, D.C., Florida, and Pennsylvania.

But above all else, Gary was a family man. He is survived by his beloved wife, Joyce, with whom he shared a lifetime of love and memories; his daughter, Annie, and son, Zach; his son-in-law, Jason, and daughter-in-law, Sally; and his two cherished grandchildren, Gianna and Mila, who brought him immeasurable joy and filled his heart with pride.

His wife, children, grandchildren, and extended family of his in-laws and their children were the center of his world. He treasured every moment spent with them, including with his furry family members - his beloved dog, Dunkin and granddogs  Rocko, Oakley, Tater, and Mabel. His love for all of his family was unwavering, and the memories he created with them will remain a lasting part of their lives.

Gary had a special gift for connecting with people. He was kind, genuine, caring, and quick to share a smile or a laugh. He had a way of making people feel comfortable, valued, and important. Those who knew him will remember not only the wisdom he shared, but also his humor, warmth, and the way he could brighten a room simply by being in it.

Gary leaves behind a legacy that extends far beyond his years with his family and in the classroom. His daughter Annie is now a principal in BCPS, and his son Zach is a nurse anesthetist in NYC. Gary also leaves behind generations of students whose lives he influenced, educators whom he inspired, friends who were fortunate to know him, and, most importantly, a family who will carry his love and memory with them always.

His family takes comfort in knowing that Gary spent his life doing what he loved—teaching, connecting with others, making people laugh, and leaving the world a little better than he found it.

He will be deeply missed, lovingly remembered, and forever cherished.

In lieu of flowers, please consider donating to one of the following organizations in memory of Gary.

TABCO KidCare Donations:
KidCare is a Baltimore County Public Schools / TABCO organization through which 100% of the money raised goes to students in BCPS who are in need of school supplies.

https://donate.stripe.com/00w4gzd3Eb0D02V4CAbII05

BCPS Education Foundation Donations:

The Education Foundation of Baltimore County Public Schools, Inc. is dedicated to being a champion for the school system through advocacy, fundraising, and programming.  The Education Foundation works to ensure that BCPS students, educators, and school communities have the resources they need to reach their full potential.

Option # 1:

·       Visit: https://educationfoundationbcps.org/
·       Click on GIVE
·       Complete the Donate Today!
·       Donation Designation = In Honor of Gary W. Caldwell

Option # 2:

·       Please make a check payable to The Education Foundation of BCPS, Inc., and mail to The Education Foundation of BCPS, Inc, ATTN: Cindy Whitcomb, 105 W. Chesapeake Avenue Suite 401-402, Towson, MD 21204, Memo: In Honor of Gary W. Caldwell

Option #3:

·       Stock Transfer and ACH Transfers options are available.  Please contact Cindy Whitcomb, Adm/Fiscal Assistant cwhitcomb@bcps.org.