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Loretta M "Lil" Oliva
July 29, 2026

Obituary

Loretta M. (Cullinane) Oliva, 88, affectionately known to family and friends as "Lil," died Wednesday, July 29th in Notre Dame Healthcare Center surrounded by her loving family.

She leaves her husband John Oliva with whom she would have celebrated their 66th wedding anniversary on August 6th; two sons, John M. Oliva and his fiancee Anne Curley of Swampscott and Thomas A. Oliva and his wife, Kimberly of Rutland; two daughters, Margaret L. Kiley and her husband, Timothy of Woburn, and Jeanne M. Oliva and her wife, Colleen Hopkins of Bristol, RI; her sister, Lorraine Cullinane of Peabody; six grandchildren, Elizabeth Liimatianen and her husband, Scott, Joseph Oliva and his wife, Maura, Thomas Oliva Jr. and his wife, Allison, Kevin Kiley, Kathleen Kiley, and Erin Kiley; three great grandchildren, Ava, Ari, and Noah; and several nieces and nephews. She was predeceased by her brother, Edward and three sisters, Pearl, Eleanor and Mary.

She was born in Concord, MA the daughter of Edward and Loretta (Shattuck) Cullinane. Lil was a graduate of Concord-Carlisle High School before continuing her education at Fitchburg State College. During her college years, she was active in sports, the Newman Club and the Tokalon Society, of which she was honored to be elected president, reflecting her commitment to scholarship, leadership, and service. During these active and busy years, she also met John, with whom she spent the rest of her life.

She dedicated nearly 20 years to Friendly's Restaurant in Tatnuck Square, where she became a familiar and welcoming face to many customers. Her strong work ethic and friendly personality also led her to positions at Lederman's Bakery, Arthur's Bagels and Friends, and the Bagel Inn. No matter where she worked, Lil made lasting friendships with her customers, who appreciated not only her exceptional service but also her outgoing personality.

An avid traveler, Lil embraced the world with enthusiasm and curiosity. She fulfilled the remarkable goal of visiting all 50 states and traveled to more than 50 countries across the globe. Her adventures brought her to unforgettable destinations including Antarctica, Machu Picchu, Ireland, Russia, China, and countless other places that enriched her life and provided stories she loved to share.

At home, Lil found joy in knitting and lovingly handcrafted sweaters for family and friends, each stitch made with patience and love. She was deeply devoted to her children and was always their biggest supporter. Whether coaching her daughters' softball teams, through Jesse Burkett Little League or cheering from the sidelines and pool-side at their many activities and accomplishments, she was their greatest fan, encouraging them every step of the way.

Her faith was an important part of her life. Lil was a devoted member of Blessed Sacrament Church and previously an active member of St. Charles Borromeo Church, where she generously volunteered as a CCD teacher, helping to guide and inspire young people in their faith.

Above all, Lil will be remembered for the way she made people feel. She was personable, adventurous, and outgoing, with an infectious enthusiasm for life that drew people to her wherever she went. She found joy in meeting new people, exploring new places, and creating lifelong memories with those she loved. Her generosity, compassion, and spirited nature leave a legacy that will live on in the hearts of her family, friends, and all who had the privilege of knowing her.

Lil's family will forever treasure the love she shared, the adventures she inspired, and the example she set of living life to its fullest.

Her funeral is Thursday, August 6th from O’CONNOR BROTHERS FUNERAL HOME, 592 Park Avenue with her funeral Mass at 11:00 a.m. in Blessed Sacrament Church, 551 Pleasant Street. Burial will follow in Worcester County Memorial Park, 217 Richards Avenue, Paxton. Calling hours are Wednesday, August 5th from 4:00 until 7:00 p.m. in the funeral home. In lieu of flowers memorial contributions may be made to the Alzheimer’s Association, 320 Nevada Street, Suite 201, Newton, MA 02460 or to the Diocese of Worcester, c/o Partners in Charity, 49 Elm Street, Worcester, MA 01609.

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O'Connor Brothers Funeral Home
592 Park Avenue
Worcester, MA 01603
508-754-2431