Sheila Ann Pinkerton

Portland – Sheila Ann “McCaffrey” Pinkerton entered this world on November 9, 1934 at the former Maine General Hospital in Portland Maine, the daughter of Philip Patrick and Ann Griffin Foley McCaffrey. She left this world at the same location, the current Maine Medical Center on January 11, 2026.

She lived the first quarter of her life on Victoria Street in East Deering, first in her parents home and then she and her husband purchased a condemned house down the street and lovingly fixed it up. Her early years were filled with physical struggles resulting from a cerebral hemorrhage at birth and she endured numerous surgeries to enable her to walk relatively normal. Her childhood featured many adventures on and around Martin’s Point with the neighborhood kids, but one adventure stood out; painting her fathers black car with white house paint she’d found. Her grandmother just stood in the doorway saying “Oh Dear, what is Phil going to say?” She loved retelling that story.

Her family spent much time on the west shore of Sebago Lake where aunts and cousins had camps. Time was also spent at Higgins Beach every summer and till the end, she loved going to the shore to listen to the waves and feel the salt air on her skin.

She graduated from Portland High School with the class of 1954 and was a proud lifelong Bulldog supporter, though all three of her children went to Deering.

She met the love of her life, Raymond Everett Pinkerton, in her mother’s living room in 1956 on a blind date set up. Raymond was from West Virginia but was stationed in Portland with the United States Coast Guard on the USCG Cutter Acushnet. Their first home together was an apartment on Brighton Avenue for 1 day, until Ray shipped out on ice patrol duty. Their original wedding date was March 5, 1957, but it was moved up a day due to Raymond’s orders to ship out. A photo of Sheila kissing Raymond at the Maine State Pier as the ship was about to leave was featured on the front page of the local papers that day.

Their first child, Ann Marie, was born the following year and they set up their home down the street from her parents. Ann was joined two years later by Philip Paul, who sadly died of SIDS three months later. This death haunted Sheila till her last day and she never lost that pain. Later that year, Ray was reassigned to the Loran Radar Station on Kodiak Island, Alaska. Her mother was horrified and didn’t want her to go, but Sheila needed to be at her husbands side and away from the grief that still lingered in the house on Victoria Street. Sheila always said that the years spent in Alaska were her happiest. It was there that Phyllis Margaret joined the family. They returned to Portland Maine several months before the great earthquake shook the area destroying much of the community, including their home.

After several years in Portland, Raymond was reassigned to the US Coast Guard Academy in New London, Connecticut until his medical discharge from active duty in 1968. It was here that Peter John joined their family.

In 1970, they returned to Portland and settled on Summit Park Avenue for the next 50 years, making many good friends in this close knit community.

She was a proud Irish American and delighted in telling anyone that she was a just a “Stubborn Old Irish Woman”. She and Ray were able to take several trips to Ireland in her later years and each one was a joy. They also traveled around the East Coast and throughout Maine in their motor home as part of the Good Sams Club and Lake Region Wanderers.

The love of her life passed away in 2010 and initially Sheila struggled as she suffered from many physical ailments her whole life. Mobility was difficult. However, through sheer grit and determination, she stayed in this home with help from others for 10 more years, a fact she was most proud of. She loved to tend her flower gardens and swim in her pool (with help) and take scooter rides around the neighborhood and down to Shaw’s. A lifelong knitter, it was during this time that she took up the craft with a renewed energy, making hats; first for newborns at Maine Medical Center and then for Cancer patients at the Maine Center for Cancer Medicine in Scarborough. At last count, the number of hats she produced was numbered near a thousand. Her hats are still seen on strangers walking the streets of Portland.

Her final years were spent with a loving community at the Cedars in her old neighborhood in Portland, first at the Osher Inn Assisted Living and after breaking her hip from a fall in December of 2023, at the Hoffman Center. She was lovingly cared for by the staff of this community and she found renewed energy to continue her knitting of hats for many of the staff members and their families. After her fall, her ability to knit left her and she struggled with the final hat for two years. It still sits in her knitting basket waiting to be finished.

After enduring a lifetime of physical ailments and illnesses, including beating Covid-19 when nobody was beating it and consistently defying the odds against her, she succumbed to a combination of Influenza and pneumonia surrounded by love. Her lessons and work complete, she was able to take Raymond and Philips hands and passed peacefully and joyfully into the next world free of the bonds of her infirmities.

She is survived by her daughters, Ann Giampetruzzi (Steven) of Raymond, Phyllis Andersen (Craig) of Windham; and her son, Peter Pinkerton (Blaine Skilling) of Gray. She is also survived by four grandchildren, four great-grandchildren and one more on the way in March of this year. She will be remembered for her mischievous laugh, her unfiltered tongue, a fierce determination, her sharp wit, and her love of all things Irish and cardinals.

Friends and family are invited for a time of remembrance and visitation at the new Conroy-Tully Walker Cremation, Funeral & Gathering Center, 300 Allen Ave, Portland on Friday, January 23, 2026 from 4-7 PM. A Mass of Christian Burial will be celebrated at St.Pius X Church, 492 Ocean Ave, Portland on Saturday, January 24, 2026 at 11 AM. Interment will immediately follow at Calvary Cemetery in South Portland.

In lieu of flowers, people are encouraged to donate to the St. Jude’s Children’s Research Hospital at 501 St. Jude Place, Memphis, TN 38105, or The Cedars Care Champion Fund at 630 Ocean Avenue, Portland, Maine 04103.