Bonnie Jean Olson, a woman defined by her devotion to family and her lifelong commitment to her community, passed away peacefully on April 1, 2026, at the age of 85. Born in Mountain Grove, Missouri, she was the daughter of the late Otto and Beatrice (Green) Ristow and the beloved wife of 62 years to the late Jack Michael Olson, who predeceased her in November 2025.
After graduating from Culver-Stockton College—where she was a proud member of the Sigma Kappa Sorority—the two married on August 10, 1963. Together, they built a home in Holliston anchored by laughter and service.
Though she began her career at Liberty Mutual, Bonnie found her true calling in the classrooms of Holliston Elementary School. As a longtime paraprofessional, she touched the lives of countless students before retiring in 2001. Her dedication to children extended far beyond the school day; she was a beloved Sunday School teacher, Brownie leader, and softball coach.
Bonnie was a woman of many passions. In her younger years, she was a fixture in the local social scene, active in the Curtaintimers, the Newcomers Club, and the Congregational Church. She was an avid bowler and golfer who never turned down a game of cards or Mahjong. In later years, she found joy in simpler pleasures: watching the birds, playing bingo, and conquering complex jigsaw and crossword puzzles. A voracious reader of romance novels, Bonnie could often be found scouring the aisles of Target or the local library for her next great story.
Of all her roles, “Grandmother” was perhaps her favorite. A fixture in the stands at her grandsons’ sporting events in Medway, she was their most spirited and vocal fan.
She is survived by her three daughters: Sara Bailey and her husband, Jefferson; Michelle Olson; and Marci Murphy and her husband, Kevin. Her legacy lives on in her three grandsons, Brian and Sean Murphy, and Jackson Bailey.
Visitation will be held on Monday, April 20th, from 10 am-12 pm at Chesmore Funeral Home of Holliston, 854 Washington St. www.ChesmoreFuneralHome.com A funeral service will follow in the funeral home at 12:00 p.m. Private burial will take place.
