Howard Emmett "Cutter" Drewry Jr.

Howard Emmett Drewry Jr, also known as "Cutter" and "Pops" died peacefully in his sleep on November 14th, 2024. He was born July 24th, 1928 to Howard Emmett Drewry Sr. and Edith Warren Drewry.
He was the oldest of five sons. Cutter was raised on his parent's farm, helping out at an early age. He nurtured a life-long love of farming, cultivating a lifetime of knowledge and common sense. With his death, we have lost a library of rural know-how. Known for his kindness, generosity and athletic abilities, Cutter was able to attract one of Wakefield's leading bachelorettes, Miss Joan Pittman. They were married January 27th, 1952. They raised two children, Gayle Drewry Simms and Michael Howard Drewry. The life they lived was similar to a Norman Rockwell painting, in that they lived in a close, tight-knit, multi-generational community that was interdependent and thriving.
Like many of his generation, he could fix and repair almost anything. He never met a stranger, he loved to tell stories, and his gentle nature was legendary. His nickname "Cutter" was given to him by Dendron Elementary School classmates for his antics at school, and it stuck for a lifetime.
His love for baseball led him to be the Wakefield High baseball coach and player during his senior year, created many memories of playing for the Town Team, and was asked to participate in Major League Baseball try-outs. Ultimately the love for his community, family and farming kept him close to home. Farming was his first passion and he also worked in the family business, Pittman Chrysler Plymouth, for many years. He loved being a Husband and Father, he coached little league, volunteered at the fire department, was a member of the Ruritan Club, loved car racing, and particularly loved his Washington Redskins. During his retirement, he helped his son Michael run Drewry Farms.
He is survived by his wife, Joan Pittman Drewry, daughter Gayle Drewry Simms; son, Michael Howard Drewry (Amy); five grandchildren, Chris (Jennie) Simms, Sara (Jake) Harsh, Kristen Drewry, Carla (Aaron) Thompson, and David (Margaret) Drewry; five great grandchildren, Oliver, Ezra, Tucker, Graham and Demi; brothers James (Nancy) Drewry, William (Rosalie) Drewry, Emmett (Lizzie) Drewry, and Thomas (Joanne) Drewry and numerous nieces and nephews. A role model, and loved by all who met him, he will be greatly missed.
We would like to especially thank Mary Beth Vincent of Crater Hospice Care for her love and devotion to our precious Cutter in his last months of life
Funeral Services will be held at 11:00 a.m. on November 19, 2024 at Spring Hill Congregational Church. Graveside services will be after at Wakefield Cemetery. In lieu of flowers, please make donations to The Wakefield Foundation, P.O. Box 8, Wakefield, VA 23888. R.W. Baker & Co. Funeral Home and Crematory, Wakefield Chapel is serving the family. Condolences may be registered online at RWBakerFH.com.