Sheila (Holt) Drain, 67, passed away Thursday December 7, 2023 after battling health issues for the better part of the year.

The devoted wife and mother is survived by her sister Mary Ellen, her brother Tom (Sue); her three sons Sean (Kendra), Joseph (Elitza), and Stephen (Katie); and her granddog, Rudy. Sheila was predeceased by her brother Stephen; her parents, Mary and Alfred; and her amazing husband, Dennis.

Born and raised in Dorchester, Sheila’s Irish-Catholic family eventually moved to Milton and she graduated from Milton High School in 1974 where she excelled in gymnastics and started dating her future beloved husband, Dennis. She went on to attend Curry College (Class of 78) and ultimately settled back in Milton to raise her family.

After running a daycare out of her house for the better part of a decade, Sheila went on to teach students with special needs in the Boston Public Schools for 27 years where she educated thousands of children, mentored young teachers, and was revered by her peers as one of the top educators in the state. When Sheila wasn’t teaching, she remained extremely active in the Milton community. She coached many years for Milton Youth Soccer, volunteered for 20+ years in the Milton Learn to Skate program, and joined community planning committees to help raise money and build playgrounds and parks for the town.

To say that she balanced her “hobbies” well with her teaching career and community involvement would be a dramatic understatement. Sheila was prolifically talented; her gardens belonged on HGTV, her cooking skills were worthy of a Michelin Star, and she was an award-winning quilter. Out of all the things Sheila excelled in, she may be most fondly remembered as a tremendous role model, a great friend, a caring sister, a loving wife, an exceptional mother, and one of the most resilient and kindest people anybody knew.

Visitation at Dolan Funeral Home, 460 Granite Avenue, EAST MILTON SQUARE, Thursday, December 14 from 8:30 – 11:00 am. A Mass of Christian Burial will be celebrated in Saint Agatha Church, Adams Street at 11:30 AM. Relatives and friends invited.

In lieu of flowers, we kindly ask that you consider making a small donation to the Special Olympics Massachusetts, a cause that was close to Sheila’s heart. Your contribution will help honor Sheila’s memory and make a positive impact on others.