Deborah O'Connor

West Boylston/Holden - Deborah O'Connor, 85, passed away peacefully on March 28, 2026, at Bridges by EPOCH in Hingham. For 51 years, she was the loving wife of the late David C. O'Connor, who predeceased her in 2020.

Born in Worcester, she was the daughter of Bernard J. and Eleanor A. (Laing) Clifford. After being raised in Worcester and beginning her career there, she lived 26 years in Holden, 7 years in Harwich, 15 years in West Boylston, and the last 2 years in Hingham. An accomplished student, she attended Notre Dame Academy before earning her bachelor's degree from Trinity College and later completing a master's program at Assumption University. She continued her studies through graduate coursework at Clark University and Harvard University.

Deborah met her future husband, David O'Connor of Worcester, while teaching at Burncoat Junior High School in Worcester. After a brief courtship, they were married on June 21, 1969, at Our Lady of Rosary Church and lived in Worcester for several years before moving to Holden, where they raised their four children.

A devoted English teacher, she spent the first 6 years of her career at Burncoat High School before spending 18 years at Wachusett Regional High School, where she retired. She took great pride in preparing AP English students for college success, challenging them to read analytically and write persuasively. Beyond the classroom, she generously gave her time. In the 1980s, she was an active room mother at Chaffins School, a Cub Scout den mother for her sons, and a founding member of the Holden Educational Assistance for Learning Disabilities (H.E.A.L.D.). This local volunteer-led nonprofit organization provided educational resources, advocacy, and support services for children with learning disabilities. In later years, she contributed her time to organizations including VNA of Cape Cod and the Harwich Public Library and served as Vice President of the Angell Brook Women's Club.

She found great joy in music (Jim Croce and Gordon Lightfoot), running, gardening, cooking, and reading, but above all, she cherished the time she spent with her children and grandchildren.

Deborah will be lovingly remembered and missed by her four children, Sean O'Connor of Watertown, Kevin O'Connor of Worcester, Elizabeth O'Connor and her partner Ethan Brannon of Altadena, CA, and Sarah McSweeney and her husband David of Norwell; her sister Elizabeth Clifford of Charlestown; grandchildren, James and Mairead O'Connor, and Audrey and Katherine McSweeney: and many nieces and nephews.

In addition to her late husband, Deborah is predeceased by her brother, Lawrence Clifford, and her sisters, Margaret Clifford, Eleanor Clifford and Mary Hubert.

The family extends its gratitude to the wonderful staff at Bridges by EPOCH in Hingham for the excellent and compassionate care they gave Deborah in the final 2 years of her life.

Family and friends are kindly invited to attend visiting hours on Tuesday, April 7th from 4:00 - 7:00 PM at Miles Funeral Home, 1158 Main Street in Holden. A mass of Christian burial will be celebrated on Wednesday, April 8th at 11:00 AM at Our Lady of Good Counsel, 111 Worcester St, West Boylston, followed by interment in St. John's Cemetery in Worcester.

In lieu of flowers, donations in Deborah's memory may be made to the Foundation Fighting Blindness, online at https://www.fightingblindness.org/ or by check at P.O. Box 45740, Baltimore, MD 21297-5740. Checks should be made payable to "Foundation Fighting Blindness," and donations should please reference Deborah O'Connor.

To leave a message or share a memory please visit www.milesfuneralhome.com