Ann Halstead Obituary

Ann Halstead

Our wonderful family just lost one of its most cherished members. Our beloved, Ann M. (Gibbons) Halstead (born May 20, 1932 in Boston, Mass.) passed away on Friday, March 19, 2021 at home on her beautiful Penny Lane Farm in Danville, Vermont surrounded by her loving family. We are all so blessed to have had this incredible, truly “great woman” in our lives. She has touched so many of us in different ways with her free spirit and love of life. Her presence will be deeply missed, but her loving spirit will live on in our hearts forever.

All you had to do was meet Ann just once to feel inspired by her warmth, energy, athleticism and zest for life. She effortlessly inspired all of us who knew and loved her. She was a mom extraordinaire to 10 children and lived life to the fullest. She often would say… “Life is Not a Dress Rehearsal…Go & Live it!” She loved her family, her animals and life with passion and respect.

Sadly, she leaves her 10 children: Susan Galipeault and husband Larry of Danville, Vt., and Fitchburg, Mass., Ann Marie Trapasso and husband Anthony Jr. of Sterling, Mass., Julie Grenier of Westminster, Mass., Robert L. Halstead Jr. and wife Amy of Fitchburg, Mass., Linda Story and husband Mike of Gloucester, Mass., Barbara Halstead-Gallinaro of Pembroke, Mass., Donna Halstead of Baldwinville, Mass., Brian Halstead of Worcester, Mass., Kevin Halstead and Gina of Westminster, Mass., Michael Halstead and wife Julie of Leominster, Mass.; & 17 adoring grandchildren, Sarah, Daniel Robert and Amy Galipeault, Alexa and Anthony Trapasso III, Jon, Christopher and Andrew Grenier, Macie Halstead, Alicia, Julianne and Alfred Gallinaro III, Michael Jr., Alden and Jacob Robert Halstead; Ava and Caden Halstead and four adoring great-grandchildren, Paige, Adelyn, Maryanne & Olivia Ann.

She also leaves her loving brother Paul Gibbons and her amazing sister Mary Gibbons along with many cousins, nieces, nephews and close extended family members that meant the world to her as well as her four-legged best friends, “Missy,” her 30-year-old Arab mare, her adoring Australian Shepard “Ashby” along with her beautiful “free-range” chickens.

She was predeceased by her beloved husband, Robert L. Halstead in 2010 and are certainly together again “dancing their Irish Jig.” She was also predeceased by her parents, Dr. Joseph F. Gibbons and Helene (McDonald) Gibbons, her brothers Joseph, Bill, Peter Gibbons and her sister Helene Dunn as well as her son-in- law David Grenier.

As a young woman, Ann was honored to be one of the first women in US history asked to join the Olympic horse jumping team. She was also proud to be inducted into the Westwood High School Athletic Hall of Fame. She often shared memories of how special and unique it was to have been one of the 19 girls to attend Stonehill College’s first Co-ed class in 1951, while earning her B.S. in English. It was at Stonehill where she met and fell in love with her loving husband of 54 years (before his passing). Robert “Bob” & Ann founded “Halstead Insurance Agency” in Fitchburg, Massachusetts and settled down there, to raise their 10 children. Ann shared her expertise and love of horses by encouraging many young equestrians on a similar path. Ann’s equine accomplishments were a perfect fit to form the North County Riding and Driving Club in Central Massachusetts and she continued teaching riding lessons and organizing competitive trail rides for so many, young and old.

Ann’s thirst for adventure taught us that life is not to be taken for granted. She led by example by finding joy in each and every day; belting out a tune just because it felt so good and embracing each day as if it were your last. Heaven has a new horseback riding, Irish jigging, funny, beautiful angel who is sure to shake things up there.

It is difficult to imagine a world without her in it, but her family promises to sing loudly, dance often and embrace every single day in a positive way. “No regrets!!”

A Private family ceremony was held this past Tuesday at Ann’s beloved Penny Lane Farm in Danville, Vt. and a Private Funeral Mass will be held at St. Bernard Parish in Fitchburg, Mass. The family invites the public to join them for Ann’s burial at St. Bernard Cemetery, Fitchburg, Mass. on Saturday, May 8 at 10:15 a.m.

We truly thank Sayles Funeral Home of Saint Johnsbury, Vermont for all your kindness & unending support as well as Smith-Mallahy-Masciarelli Funeral Home of Fitchburg, Massachusetts for their help & guidance with Ann’s Funeral Services.

Please visit to leave your thoughts and tributes and to view our online memorial to our amazing Mom ……Ann M. (Gibbons) Halstead.

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