Roberta “Bobbie” (Canning) Skillin of Dorchester Lower Mills and Cotuit died peacefully at home on November 13, 2026, surrounded by her loving family, after a courageous battle with cancer.

Born in Boston, MA to Andrew and Lillian (McNulty) Canning of Dorchester and Cotuit, she is survived by her husband of 52 years, D. Michael Skillin and her five children: David (Maureen) of Milton, Gregory (Melissa) of Dorchester, Christopher (Sarah) of Milton, Elizabeth (Gregory) Everson of Dorchester, and Matthew (Kayla) of Franklin. She was the proud Grammy and Yaya to Maeve, Aidan, Andrew, Lila, Gregory, Avery, Danny, Jackson, Lillian and Connor.

Bobbie was predeceased by her sister Nancy Lee and brother-in-law Joseph Lee of South Boston and her sister Joan Lane, and brother-in-law Charles Lane of Bradford. She is survived by her brother-in-law Mark (Helen) Skillin of Wallingford, CT, and her sisters-in-law Judy and Nancy Skillin of Medfield, and many nieces and nephews.

Bobbie was a lifelong parishioner of Saint Gregory’s Church where she was baptized, confirmed and married. She was a graduate of Saint Gregory’s Grammar School, Saint Gregory’s High School, and Boston Business School.

Bobbie worked as a legal secretary in Boston until the birth of her first child. She became a stay-at-home mother, raising her five children while working part time at Star Market; a position she held for 29 years. When her youngest son started high school, Bobbie went to work for the Boston Public Schools in the Special Education Department from where she retired in 2018. While working for BPS, she took great pride in finding the best school placements for students with special needs and best job placements for special educators.

Bobbie’s dedication extended beyond her family and work; she volunteered her time with many community organizations such as the Saint Gregory’s Ladies Solidarity, organizing the Saint Gregory Grammar School 75th reunion, serving as a Eucharistic Minister, a CYO leader, a Girl Scout leader, a coach for the All-Dorchester Sports soccer (Bumble Bees) team, treasurer of the Saint Brendan/Saint Ann bowling league and running the Saint Gregory’s Sunday night bingo.

Bobbie’s love and incredible talent for flower arrangement and décor led her to be the unofficial church decorator for the holidays. She was known for her amazing bow-making, and always had the most impeccably wrapped presents.

Bobbie never missed her children’s sporting events, and that continued with her grandchildren; she was their biggest fan and cheerleader. She became an avid fan of hockey, soccer, softball, basketball, Gaelic football, rugby, football, field hockey, swimming, gymnastics, dance recitals, and musicals.

Bobbie’s love for Cape Cod began as a child, in Cotuit, at the house that her father built. She was happiest creating Cape memories with her family; she especially enjoyed beach days at Riley’s Beach with her children and grandchildren. Her perfect beach day included trips down the lazy river, adventures to the Point, and surfboard sessions (which usually involved all the children on the beach taking turns jumping off of the surfboard).

Bobbie was also lucky enough to have her lifelong friend by her side during her cancer fight. Her family would like to give a special thank you to her best friend, Donna Regan, for driving and being with Bobbie during her many doctor’s appointments and treatments.

A Mass of Christian Burial will be celebrated at Saint Gregory Church, 2223 Dorchester Avenue, Dorchester Wednesday November 18 at 11:00 AM. Family and friends invited. Visiting hours at Dolan Funeral Home, 1140 Washington Street, DORCHESTER LOWER MILLS, Tuesday November 17 from 4-8 PM. Interment Cedar Grove Cemetery

In lieu of flowers please donate to Saint Gregory’s Church, 2223 Dorchester Avenue, Dorchester, MA, 02124.