School 10

Ann Sherwood (Wiley) Olkkola

November 12, 1942 ~ August 29, 2021 (age 78)


Ossipee, NH


Ossipee, NH - Ann Sherwood (Wiley) Olkkola, 78, died Aug. 29, 2021, surrounded by family and friends. 

Ann was born in Ayer, Mass., November 12, 1942 to Joseph and Beverly (Sherwood) Wiley. She graduated from Dennis Yarmouth High School in 1960 as a member of the National Honor Society, graduated from Vermont College with an Associates degree in 1963 and Johnston State College with a Bachelor's degree in 1965.  She married Peter Olkkola in 1967 and they were married for 42 years until his passing in 2009.

 Ann began her career as a first grade teacher at South Yarmouth Elementary school before she and Peter moved first to Wakefield, NH where they ran the Wakefield Inn and then to Ossipee, NH and owned Moulton’s Store.  Ann returned to the education field as a Special Ed teacher at Ossipee Central School.  In 1987 she started as a library associate at Kingswood Regional High School. Ann loved KRHS, seeing more than 5,000 students pass through the school over her 33 year career. She was a founder of the Faculty and Staff Scholarship Fund (which will now be named in her honor) which has raised and given away tens of thousands of dollars to deserving KRHS students.  Working closely with student leaders to guide and develop their leadership and organizational skills, Ann was the co-founder of the annual Christmas Craft Fair, raising the foundational funds for the scholarship.   Ann garnered respect from her peers and administrators being recognized as “the moral compass of our school community” according to Director of Library Media Services Karen Libby.  She was also a long time member of the National Education Association.

 In her private life, Ann and Peter lived on a farm in Ossipee, NH raising their three sons there and producing maple syrup for decades.  Ann was passionate about antiques as both buyer and seller and had limitless enthusiasm for reading and spending time with her grandchildren.

 Ann is survived by her three sons and daughters-in-law and nine grandchildren. Jared and Lucy Olkkola and daughters Phoebe, Emmy, Lottie and Lila of Dover, NH; Justin and Sarah Olkkola and children Tyler and Alexis of Ossipee, NH and Jake and Michelle Olkkola and children Caroline, Jed, and Jocelyn of Newark, DE; a brother and sister-in-law David and Karen Wiley of Tuftonboro, NH and Leesburg, FL; a sister-in-law Connie Munro; a niece Kate Prendergast of Rollinsford, NH, and many cousins, nephews and loving friends.

 SERVICES: Calling hours will be held on Friday, September 17th from 5 to 7 p.m. at Lord Funeral Home, Wolfeboro, NH.  The family requests that those attending wear masks and social distancing be observed.

 IN MEMORY: The newly named Ann Olkkola Memorial Fund will provide scholarships to Kingswood students who are pursuing a career serving others and will also support a memorial reading garden (also named in her honor) located outside the Kingswood Library Media Center.

 In lieu of flowers please make donations to the Ann Olkkola Memorial Fund ℅ Kingswood Regional High School 396 S Main St, Wolfeboro, NH 03894 or Cornerstone VNA 178 Farmington Rd, Rochester, NH 03867.

To send flowers to the family or plant a tree in memory of Ann Sherwood (Wiley) Olkkola, please visit our floral store.


September 17, 2021

5:00 PM to 7:00 PM
Lord Funeral Home, Wolfeboro, NH
Rt. 28
Wolfeboro, New Hampshire 03894

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