Robert Harold Montgomery, beloved husband, father, grandfather, and great-grandfather, passed away peacefully on November 7, 2025, in Winchester, Virginia, at the age of 90. Born on October 26, 1935, in Harrisville, Pennsylvania, Bob lived a life marked by deep devotion to family, a strong work ethic, and a quiet spirit of adventure that touched all who knew him.

He is survived by his three sons: Robb (Ann), Jeff (Christel), and Don (Pam); grandchildren Robert Harold Montgomery III, Laura Elizabeth (John) Roth, Sarah (Robert Vaughan) Montgomery, Emma Montgomery, and Natasha (Lauren Hartzell) Montgomery; and great-grandchildren Emily Elizabeth Roth, John Harold Roth, Alice Ursula Vaughan, and Wren Anne Vaughan — each of whom held a special place in his heart.

Bob was preceded in death by his parents, Virginia and Harold (“Smack”) Montgomery of Grove City, Pennsylvania, and by his beloved wife, Elizabeth Ann Montgomery. Together, Bob and Elizabeth shared a lifetime of love, partnership, and adventure. After a successful career with Bell of Pennsylvania and later Verizon in Herndon, Virginia, they retired to Hilton Head Island, where they embraced island life and formed many lasting friendships.

Following Elizabeth’s passing in 2014, Bob returned to Winchester to be closer to family. He spent his final years at The Willows at Meadow Branch Assisted Living, where he was known for his gentle spirit, quick wit, model building, and caring nature.

Bob will be remembered for his integrity, his warmth, and the joy he brought to every gathering. He leaves behind a legacy of love, resilience, and cherished memories that will continue to inspire all who knew him.
A memorial service will be held at a later date.

In lieu of flowers, donations may be made to a charity of your choice in Bob’s memory.