Raymond Upshaw, 86

Meet Raymond Upshaw, 86

Born in Windsor, Nova Scotia, in 1939, Raymond grew up in a close-knit community where simple joys shaped his childhood. He could often be found riding bikes or walking the roads with friends, soaking in the freedom and laughter of small-town life. Those early years grounded him in the values that would define him for the rest of his life: family, community, faith, and humility.

Raymond built his life around these values. He and his beloved wife were married for 61 years, raising five children together in the home where they created decades of memories with their grandchildren and great-grandchildren. Their door was always open, their kitchen always warm, and their lives deeply intertwined with those around them. A pillar of the Three Mile Plains community, Raymond’s kindness touched countless families and became a defining part of who he is.

Raymond’s working life carried that same spirit of resilience and determination. He became the first Black driver for Allied Van Lines in Montreal, an accomplishment that speaks to both his perseverance and his role as a quiet trailblazer. Though he found work opportunities in Montreal that weren’t available back home, his heart never left Nova Scotia. Eventually, he returned, choosing family over convenience, and continued his career at Minas Basin Pulp and Paper and then CKF in Hansport. His greatest pride has always been keeping his family united and rooted.

Outside of work, Raymond found joy in the little things, yard sales, vintage treasures, and especially old cars. His grandchildren often describe him as someone with a keen eye for history and a soft spot for craftsmanship. But nothing brings him more joy than his role as a grandfather. His faith and his family remain at the center of his life, and he has long served as a Deacon at Three Mile Plains Baptist Church, a role that reflects the deep respect his community has for him.

This past year, Raymond experienced a profound loss with the passing of his wife, his partner of six decades. In the days following her funeral, he shared a wish he had quietly carried in his heart for years: to take a helicopter ride just once and see, from above, the home, church, and community where they built their life, raised their children, and created 61 years of memories together. What began as a quiet, long-held dream now carries even deeper meaning following the loss of his beloved wife.

For Raymond, this was more than a new experience. It was a chance to reflect, to heal, and to feel close to his wife again, to see from above the life they built together and the community that has shaped so much of who he is. Those who know Raymond describe him as quiet, humble, and always thinking of others, the kind of man who would never ask for something like this for himself.

Yet this moment brought him peace, awe, and a quiet sense of connection that words cannot fully hold. For a man who has spent his life lifting others up, this helicopter ride became a moment of being held in return by the very community he gave so much to.

Special Thanks: Vision Air Services Inc. for always going above and beyond for our wish recipients.

Photography: Tori Weeks