Cover photo for Cheryl G. Olson's Obituary
Cheryl G. Olson Profile Photo
1944 Cheryl 2021

Cheryl G. Olson

June 9, 1944 — March 3, 2021

WEST BOYLSTON-Cheryl Gail (Sherry, Mom, Babe, Nana) Olson (Hamilton), 76

Sherry Olson, beloved wife, mother, grandmother passed away peacefully at Blaire House of Worcester on March 3rd, in the morning, after a long illness.

Sherry was born in Clinton on June 6th, 1944. She was the first child and only daughter of Cecilia (Pierce) and Roy Hamilton. Her family, including brother David, would move to Boylston when they were young. She was untimely predeceased by her baby brother in 2015.

She graduated from West Boylston High School and subsequently earned her teaching degree at Worcester State College. She would serve her entire teaching career at Berlin Elementary, picking up two master's degrees at Anna Maria in the eighties and achieving the position of Principal at the school she loved so deeply and was so fiercely passionate about.

On July 30, 1966 Sherry Hamilton married Allan Olson and they raised their son, Eric in Boylston and later West Boylston. Before they had Eric they traveled to the British Isles and Jamaica, and with Eric they took vacations every year to Maine, places of historical significance like Gettysburg, and fantastic big extended family trips to Disneyworld and Hawaii. Sherry and Allan, with their son and later their grandsons, spent their time creating and sharing grand experiences and adventures and that was the spirit Sherry exemplified in life. Everything was interesting and could and should be learned from.

Eric had two sons, Tyler and Elijah and Sherry retired from her beloved teaching to be a full time Nana. Sherry loved her family with all her heart and for 24 straight years she and Allan came to Maine for the Christmas holiday. Sherry loved Christmas above all things and those holiday experiences they had with their son and grandsons were most of the year in the making and always involved gifts of an unusual or uncommon bent or theme which always led to many interesting conversations and knowledge.

Cheryl's life is marked and remembered for her love for her family and the generosity and giving that drove her in all things. She was an outside the box teacher and instilled in her loved ones a sense of community and humanity that would deeply influence the path of her only child, and many others. She appreciated history and delighted in discovering obscure facts and unexpected truths, the kind of thing you only hear on the tour at the actual place. She took joy in recreating old recipes from Grandma's cookbook, or exposing her child and grandchildren to a grand view, exotic location or new experience.

Sherry is survived by her beloved husband of 54 years, Allan, her son Eric, and her grandsons Tyler and Elijah. She had many cousins and missed those who went before, Jimmy, Donny, Kenny, and will be missed by Paul, Dickie and Candy. The nephews and nieces are numerous and so are their names, but they are all Pierces, ultimately and beloved cousins: Kevin and Tim, Todd and Kim, Kristi, Julie and Joel, Donny and Jay, Rebecca, Amanda, and Meghan, Leeann and Greg, Scott and Heidi, and Susan and Steven. Her love for all of them endures, and she took great joy in watching her extended family grow down through the generations, including her many, many grandnieces and grandnephews.

Her many friends unfortunately cannot be named but her teaching colleagues that became lifelong friends were very special to her and her love for them equaled her love for her own family. Her best friend Ellen Power shares that she is remembered most universally for filling time with laughter and she was a very important person to a great many people. Sherry would be very pleased with this. Trudy, Cynthia, Jean and Janet and all the rest, know that there was great joy in her life for sharing the times she shared with all of you.

Calling Hours are from 2 to 4 PM, Sunday, March 7th at Fay Brothers Funeral Home, 1 West Boylston St. A funeral service will occur on Monday at 11AM in the funeral home. Burial will follow in Pine Grove Cemetery, Boylston. In lieu of flowers the family asks that a donation be made in Cheryl's memory to: Berlin Teachers Association Scholarship c/o Berlin Memorial School 34 South ST. Berlin, MA, 01503.

Finally, because of the ongoing health crisis, the family wishes it to be known that the safety of our great family and community would be of utmost importance to Sherry and in that spirit, we request that people make their best decision for themselves and their families regarding attendance at this service. Your love for her is well known and she would not want anyone to be at risk for this, in all seriousness. Your thoughts and prayers are gratefully received and have been solace in this difficult time.
To order memorial trees or send flowers to the family in memory of Cheryl G. Olson, please visit our flower store.

Service Schedule

Past Services


Sunday, March 7, 2021

2:00 - 4:00 pm (Eastern time)

Fay Brothers Life Celebration Home

1 W Boylston St, West Boylston, MA 01583

Enter your phone number above to have directions sent via text. Standard text messaging rates apply.

Funeral Service

Monday, March 8, 2021

Starts at 11:00 am (Eastern time)

Fay Brothers Life Celebration Home

1 W Boylston St, West Boylston, MA 01583

Enter your phone number above to have directions sent via text. Standard text messaging rates apply.


Visits: 10

This site is protected by reCAPTCHA and the
Google Privacy Policy and Terms of Service apply.

Service map data © OpenStreetMap contributors

Send Flowers

Send Flowers

Plant A Tree

Plant A Tree