Dr. Guy R Dillaway

March 14, 1935January 28, 2021

Dr. Guy R. Dillaway of Weston, MA, passed away January 28, 2021. Beloved husband of Barbara A. (Hutt) Dillaway; Loving father of Lance W. (Beverly) Dillaway of Weston and Gregg R. (Sarah) Dillaway of Natick; Cherished grandfather of Rebecca Dillaway (Ryan) Kring of Silver Spring, MD, Nelson (Alexandra) Dillaway of Wayland, Margaret Dillaway of Nashville, TN, Brian Dillaway of Natick and Marybridget Dillaway of Natick; Great-grandfather of Abigail Kring of Silver Spring, MD. Predeceased by his parents, Russell and Winifred Dillaway, formerly of Meriden, CT, Needham and Weston.

Born and raised in Meriden, CT, Dr. Dillaway was graduated from Meriden High School, attended Tufts University and received his doctorate degree (DMD) from Tufts University School of Dental Medicine in 1960. He and Barbara were married in 1959 and lived in Needham until he entered the U.S. Air Force (1960-1962). After spending a year working in a Boston practice, he opened his own office in Weston in 1963. This practice became Dillaway Family Dentistry, P.C. when his son, Dr. Gregg joined him in 1989. Dr. Guy continued his dental work until he retired in 2016. He was also an Associate Professor of Tufts University School of Dental Medicine from 1968-1991.

While operating his dental practice and raising a family, Dr. Dillaway was involved in several organizations, taking on many leadership and volunteer roles in his community and professional fields. He was an avid philatelist, exhibitor and judge, published philatelic literature and acted as President of Spellman Philatelic Museum in Weston for many years. He was a member of the American Philatelic Society and many other related groups and societies while representing the Museum with the New England Federation of Stamp Clubs.

An active member of the Weston Friendly Society of the Performing Arts, Inc., he was a selfless and dedicated volunteer for over 50 years. He sang and danced in many casts, built and designed sets, was the show producer in many cases, while also serving as President many years and Treasurer. In 2015 Dr. Dillaway was the recipient of the Robert E. Gard Superior Volunteer Award from the American Association of Community Theatre (AACT). He designed sets and served as a Director (and later Co-President-1987) of the Weston Drama Workshop, Inc. He was also a Mason, Shriner and member of St. Peter’s Episcopal Church of Weston.

Due to the Covid-19 pandemic, services will be private. Memorial contributions to the Shriners Hospitals for Children would be welcomed online at or mailed to Shriners Hospitals for Children, Attn: Office of Development, 2900 Rocky Point Drive, Tampa, FL 33607.


No public services are scheduled at this time. Receive a notification when services are updated.


Dr. Guy R Dillaway

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Andrea Baker

February 12, 2021

Dr. Dillaway brought joy to my family and took care of us all for decades. He is a ray of sunshine and I cherish my memories of him. May his memory be a blessing.

Thomas Smith

February 3, 2021

We were so sorry to learn of Dr. Dillaway's passing. We became patients of his when I left the Air Force back in 1971 and continued to be for over 40 years. He always had a big smile and warm handshake and we enjoyed hearing his stories. He was truly a gentle man, in his career and in life, and will be missed by all who knew him.
Tom and Joan Smith
Plymouth, MA

Carol Condon

February 3, 2021

Dr Dillaway was our family dentist for over 25 years. Always kind and caring. Condolences to the Dillaway Family.