Hopkinton (508) 435-6444   •   Holliston (508) 429-2391


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Edward Francis O'Leary Jr.

September 3, 1932 - July 16, 2022

U.S. Veteran

Visitation: Thursday, July 21st 5:00-8:00 p.m. Chesmore Funeral Home of Hopkinton

Funeral Mass: Friday, July 22nd 10:30 a.m. Saint John the Evangelist Church of Hopkinton

Burial: Following Mass in Saint Mary’s Cemetery (corner of Fiske & Central St.) in Holliston

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Edward Francis O’Leary Jr., 89, of Hopkinton, passed away on Saturday, July 16, 2022. Born in Framingham, he was the son of the late Alice R. (Cummings) and Edward Francis O’Leary Sr. He was the husband of 65 years to Mavis Angela (Murray) O’Leary.

Edward grew up in Holliston. Growing up, he enjoyed working on many farms in Holliston and throughout New England. He was a 1950 graduate of Framingham High School, where he played hockey and football. He attended Tilton Prep School (NH) and was a graduate in the Class of 1956 from Xavier University in Cincinnati, Ohio. After pursuing Army ROTC in college, upon graduation Edward joined the Army Artillery, where he served as a 1st Lieutenant from 1957-1959 and in the reserves until 1962. Edward worked as a Project Manager for the Perini Corporation from 1958-1988 in highway / heavy construction, and took pleasure in establishment and coaching of youth hockey for the Hopkinton Hornets. He was a member of Saint John the Evangelist Church in Hopkinton and after retiring enjoyed volunteering and driving the Busy Bee bus for the Hopkinton Senior Center. He was an outdoor enthusiast and loved horses. He was active in family businesses and supported all aspects of his children’s and grandchildren’s activities.

In addition to his wife, Edward is survived by 7 children, Kathryn of Clinton, Brian and his wife, Dawn of Manchester, NH, Kevin of Wayland, Daniel and his wife, Cindy of Baltimore, MD, Edward and his wife, Karen of Grafton, Alison of Worcester and Erin and her fiance, Jim of Boston. He also leaves behind his brother, Robert O’Leary and his wife, Mhel of Ormand Beach, FL, 17 grandchildren, Coretta, Mahalia, Lauren, Mollie, Sean, Owen, Elise, Timothy, Jennifer, Scott, Justine, Paige, Grace, Andrea, Gavin, Keagan and Sophia; 5 great-grandchildren, Charlie, Callie, Gabriel, Alice and Edward. He is predeceased by his brother, Richard O’Leary and his wife, Debbie, and his grandson, Matthew. He also leaves behind many nieces, nephews, extended family, many longtime friends and antique car, truck and farm equipment enthusiasts.

Visitation will be held on Thursday, July 21st from 5:00-8:00 p.m. at the Chesmore Funeral Home of Hopkinton, 57 Hayden Rowe St. www.ChesmoreFuneralHome.com A funeral Mass will be celebrated on Friday, July 22nd at 10:30 a.m. at Saint John the Evangelist Church of Hopkinton. Burial will follow in Saint Mary’s Cemetery in Holliston. In lieu of flowers, donations may be made to https://www.gofundme.com/f/memorial-hockey-fund-in-memory-of-matt-oleary