Bill Kupersmith

It is with profound sadness that we announce the passing of Bill Kupersmith, a beloved husband, father, grandfather, brother, and friend. Bill peacefully departed this world at his home in Cape Haze, FL, surrounded by his loving family, on October 25, 2026, at the age of 80. Born on May 28, 1946, in Kansas City, MO, Bill was the son of the late Louis W. Kupersmith, Jr. and Madeline (Nims) Kupersmith. His parents instilled in him the values of hard work and kindness, which he carried throughout his life. Bill graduated from Hermantown High School in 1964. His early career was marked by diverse experiences, from working at a Nursery Garden center to sailing on a merchant marine vessel from Duluth, Minnesota, to the UK. These experiences shaped his entrepreneurial spirit, and in 1972, with a loan from his father, he founded Road, Track and Trail, a successful retail business that became a staple for outdoor enthusiasts. His business acumen led him to further ventures, including the ownership of Car City, a car dealership which he and his wife, Mary, expanded to Eau Claire, WI. Bill was a man of many talents and passions. In his younger years, he was an avid racquetball and hockey player, and a dedicated motocross racer, earning five Wisconsin state championships. He found tranquility in fishing. His love for fishing and golf continued when he and Mary moved to Florida in 2003. Known for his quick wit, warm smile, and generous nature, Bill had an extraordinary gift for making others feel valued and heard. His mentorship impacted countless lives, leaving an indelible mark on all who had the privilege of knowing him. His genuine kindness and honesty were qualities that endeared him to many, creating deep and lasting relationships. Bill is survived by his devoted wife of 38 years, Mary Kupersmith, with whom he celebrated a special anniversary just days before his passing. He leaves behind his sons, Louis W. (Lee) Kupersmith IV and Noel Kupersmith, and his grandchildren, Louis W. (Liam) Kupersmith V and Macy Kupersmith. Bill is also survived by his dear siblings, Diane (Kupersmith) Berg, Madeline (Kupersmith) Westin, and Douglas Kupersmith, along with numerous friends who were touched by his spirit. A celebration of Bill's life will be held on November 1, 2026, at 3:00 PM at Bill and Mary's home, located at 245 Green Dolphin Drive, Cape Haze, FL. The family extends their heartfelt gratitude to the staff of Empath Health/Tidewell Hospice for the compassionate care provided to Bill in his final days. The family kindly requests any donations be made in Bill's memory to a charitable organization of your choice. Bill legacy of love, generosity, and kindness will forever be remembered by all who were fortunate to have known him. May his soul rest in eternal peace.