Glenwood James Dewire

Glenwood James Dewire, Jr., 75, of Winfield, PA, peacefully entered into rest on Monday, April 6 th, 2026, in Hanover, MD.

He was born on February 23, 1951, to Glenwood James Dewire, Sr., and Evelyn Virginia Dewire, and grew up in Milton, PA, with many friends that he remained close to throughout his life.

Glen left Milton to pursue a degree from Bloomsburg State College in Education, where he played defensive tackle through 1972. He followed this up with a Master’s degree in Education from the University of Virginia in 1978. In his lifetime pursuit of learning, Glen became the first member of his family to earn a college degree. He was a lifelong learner and voraciously consumed books on his favorite topics: early American history and Christianity.

Glen devoted his life to education and spent two decades working within the Chesterfield County Public School system in Virginia. As an elementary educator and principal, he made a lasting impact on his students' lives and, years later, took pride in his ability to name many of them.

Education and service formed the core pillars of his life. Glen was a generous supporter of several charities and was always willing to support his friends, family, and those in need. He gave generously of his time, volunteering with hospice and several church organizations in retirement. As a church member, he leaned on his experience as an educator to lead Sunday school classes for all ages.

Glen was an avid sports fan who rooted for the University of Virginia football and basketball teams and the Philadelphia Phillies, and enjoyed sharing his love of his teams with his many friends and acquaintances.

At the end of his life, Glen was a member of Zion Lutheran Church in Kratzerville, PA.

Glen was a proud grandfather to two grandchildren, Nolan and Felicity, of his son Philip Dewire and his wife, Kaitlyn. He is survived by his sisters, Kay Dunn and Carol Skarupsky, and her husband, Terry. He is also survived by Philip’s mother, Nancy Dewire.

Throughout his life, Glen made an impact on those he met, and he had many friends.

Family and friends are invited to celebrate Glen’s life at his favorite restaurant, Lisa’s Milltown Deli in Milton, PA, on May 2 nd at 5:00 PM.

In lieu of flowers, contributions may be made to Reach Out and Read(https://tinyurl.com/GJDinMemoriam).