Kenneth Price Callaway

MARLBOROUGH, MA – Ken Callaway passed away peacefully on April 8, 2026. He lived a long, well-traveled, and deeply fulfilling life. Ken had an uncanny ease on his road of life, striking up conversations with many people he met along the way and making personal connections. He carried a genuine curiosity about others and always seemed to have a well-timed, often humorous anecdote ready to share.

Born in Easton, Maryland to the late Anna (Stradley) Callaway and Charles Herschel Callaway, Ken grew up in Magnolia, Delaware and was provided a foundational education of work, sports, and scouting. The seeds of his future work ethic and career were sown working varied summer jobs on transportation construction sites across Delmarva with his father and brother.

A natural athlete, Ken excelled in cross country and track in high school and college. He kept up daily walks of three to four miles well into his late 80s. He was active in Boy Scouts as a child and later as a parent. He took great pride in attending his grandson Ethan’s Eagle Scout ceremony—one of many road trips he and Shirley enjoyed together.

After finding connection with Shirley during their senior year at Caesar Rodney High School, they went on to graduate from the University of Delaware, get married at Wesley UMC in Dover, and set out to build a family of their own based on devotion, curiosity, laughter, and kindness. He and Shirley relocated several times as they built their family unit of five. After moving to Verona, New Jersey in 1976, they discovered a nurturing community and actively served in social and sports organizations to support their children’s varied interests.

Ken served 7 years in the Delaware National Guard and enjoyed a 50+ year career in transportation systems engineering, traveling to over 40 countries throughout Africa, Asia, Latin America, and the Middle East. During this time, Ken and Shirley raised three children together with a steady and guiding presence. Leading by example, they focused on kindness, the positives in life, and the fortunes of family life together.

In 2012, Ken and Shirley relocated to Milford, Delaware where they reconnected with extended family and friends. He found particular enjoyment visiting with many relatives as well as monthly lunches with high school classmates. He made a habit of daily walks to the public library to read newspapers and to Shirley’s surprise, he gained an unexpected enthusiasm for yard work in retirement!

After Shirley’s passing in 2021, Ken moved one last time to New Horizons in Marlborough, Massachusetts, where he quickly settled in, forming new friendships, learning about New England, and eagerly embracing his new life. His steady stream of calls, letters, postcards, and texts with friends and family remained one of his great joys, each conversation giving him new stories to pass along.

Ken was preceded in death by his wife of 63 years, Shirley Deats Callaway. He is survived by his three children: Craig Callaway of Rostraver, PA; Dwight Callaway (Dee) of Bentonville, AR; and Cassandra Allwell (Chris) of Sudbury, MA. He is also survived by his sister June Allen (Jeff) of Dover, DE and was preceded in death by his brother C. Wayne Callaway, who is survived by Jackie Chalkley of Washington, D.C. His four beloved grandchildren—Ethan, Aiden, Sydney, and Thomas—brought him immense pride; he often marveled at how quickly they grew from toddlers underfoot into such thoughtful, engaging people. He leaves behind many beloved cousins, nieces, and nephews as well.

Ken will be very much missed.

A celebration of life event will be held in Delaware at a future date.

Arrangements have been entrusted to Dee Funeral Home & Cremation Service of Concord.