Roger Leland

Roger B. Leland

Sunday September 8, 1929 - Friday January 17, 2020
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On Friday, January 17th, Roger Leland passed away peacefully at the age of 90, at home while surrounded by the love of his family.

Roger was born in Waltham, a son to the late Rodney M. and Mabel (Conant) Leland. He was raised in Northborough and graduated Wilbraham Academy, Class of 1947. Roger attended the University of Kentucky where in 1954 he earned his BA and LL.B degrees (now J.D.) concurrently and was awarded membership to the elite Pershing Rifles fraternal organization. He was admitted to the Kentucky Bar Association in 1954, the same year he enlisted into the U.S. Army where he served as a 1st Lt. in the Army Judge Advocate General Corp (JAGS). After his honorable discharge, Roger continued his service to his country as a captain in the US Army Reserves.

In 1957, Roger started his law practice in Northborough which continues today. Roger’s expertise as an attorney afforded him admittance to practice in the Mass. Supreme Judicial Court, Kentucky Supreme Court, United States Court of Military Appeals, United States Tax Court and Supreme Court of the United States. He was a member of the American, Massachusetts, Kentucky & Worcester Bar Assns. and a lifetime member of the Kentucky Law Journal. He was instrumental in the development of a Moot Court program and funded an endowment at the University of Kentucky to assist law students. In addition to his lifelong career of practicing law, Roger continued to operate Leland Insurance, a company his father started in 1921, and maintained his real estate broker and construction supervisor licensure.

Roger earned his Masters of Law (LL. M.) in Banking from Boston University and served as Chairman of the Board of the former Westborough Bank as well as its Executive Committee, as Chairman of its Long Range Planning Committee and as a member of its Board of Directors. He later was appointed as Trustee Emeritus at Avidia Bank.

The Town of Northborough will remember Roger for the countless hours of volunteering and professional knowledge provided as he worked to better the community which he was proud to call home. For over 30 years, at various periods, Roger served on the Long Range Financial Planning Committee, and as Chair of the Appropriations Committee, Wage and Salary Classification Commission, Assistant Town Counsel and the Industrial Development Committee. In 2018, Northborough honored Roger’s longtime service to the town by bestowing to him the honor of Grand Marshal of the Applefest Parade.

He was a sportsman who loved many individual sports but golf was his lifelong passion. A member of Mid Ocean in Bermuda and of the Worcester Country Club for over 50 years, they awarded him Lifetime status. A loving family man, Roger took particular pride in his home on Bustins Island in Casco Bay, Maine. It was a special place for Roger to read, putter around on projects with all his toys, and share quality time with family and maybe a “taste” with friends. As an active participant in the Bustins Community, he served many years on the Board of Overseers, the Planning Board and the Zoning Board of Appeals. He was instrumental in future financial planning and extremely proud of his work on “The Roads Project”.

Roger is survived by his wife of 38 years, Lorraine J. (Gravelle) Leland; seven children, Mark C. Leland of Ohio, Leslie B. Leland of Ohio, James B. Leland of Framingham, Jeffrey B. Leland of Northborough, Michael B. Leland of Grafton, Jeanne L. Santella of Northborough and Pamela L. Lavoie of Millbury. He also leaves six grandchildren; Aja Leland of New Mexico, Christopher Nolin of Arlington, Connor and Brittany Leland of Northborough, Thomas and Daniel Aldonis of Millbury; and two great-grandchildren; Caulin Altman and Haedin Leland of New Mexico; many nieces and nephews, and countless others, friends and colleagues, near and far who have benefited from the pride and influence Roger’s life has made on them. Roger was preceded in death by his infant daughter, Susan, and his three siblings; Rodney C. Leland, Sarah E. Cawley and Dorothy F. Taylor.

Calling hours for Roger will be held from 4-7 p.m. on Wednesday, January 22, at Hays Funeral Home, 56 Main Street, Northborough. A funeral Mass will be celebrated at 10 a.m. on Thursday, January 23, at Saint Rose of Lima Parish, 244 W. Main Street, Northborough. Burial with Military Honors will follow in Howard Street Cemetery, Northborough.

In lieu of flowers the family would appreciate donations be made in his memory to the Wounded Warrior Project, Worcester Chapter, or given his love of education, to the institute of higher learning of your choice.
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Service Details

  • Visitation

    Wednesday January 22, 2020 | 4:00pm - 7:00pm
    Wednesday January 22, 2020 4:00pm - 7:00pm
    Hays Funeral Home
    56 Main Street
    Northborough, MA 01532
    Get Directions: View Map | Text | Email
  • St. Rose of Lima Parish

    Thursday January 23, 2020 | 10:00am
    Thursday January 23, 2020 10:00am
    St. Rose of Lima Parish
    244 W. Main St.
    Northborough, MA 01532
    Get Directions: View Map | Text | Email
    Father James Houston
  • Interment

    Thursday January 23, 2020 |
    Thursday January 23, 2020
    Howard Street Cemetery
    Howard Street
    Northborough, MA 01532
    Get Directions: View Map | Text | Email


  • Boston University
  • University of Kentucky
  • US Army


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Maria Hopkins

Posted at 06:21am
I was so sad to hear of Roger’s passing. He was a wonderful man who shared sage advice to me as a young overworked business owner and mother. He took time out if his day to send me the book “don’t sweat the small stuff” with underlined passages and handwritten notes. It still sits on my desk. He taught me that when a problem seems difficult to solve in the afternoon just sleep on it and the answer will magically appear in the morning. He was so right. I will think of him often and my heartfelt condolences go out to his family which I know was his priority and joy in his life.


Posted at 11:01am
With deepest sympathy,
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Sandra Wright

Posted at 09:52pm
Roger was a good and kind man. He was also a very good friend to my parents Hermon and Dorothy, and a sound adviser to me in my adult years. He will be missed. God Bless you Roger.

Matthew Stillman

Posted at 08:21am
To Jeff and all of Roger's family, please accept our condolences on Roger's passing. He lived an incredible life. His passing brings great sorrow but hopefully memories of his life, his accomplishments, and time with his family bring some solace.

Pam Hays Piper

Posted at 10:36am
To Roger's Family,
Please accept my sincere condolences on the passing of your father and husband. I remember the family man with love and respect. He lived life fully, freely sharing his hearty laugh, listening ear, good conversation and of course, sage advice. I hope memories bring you comfort. Hugs, Pam Hays Piper

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