Kevin Masterson Obituary, Windsor, ON Death – Family Mourns Lifelong Educator and Musician

The Windsor community is mourning the passing of Kevin Masterson, a lifelong educator, musician and mentor who died peacefully on August 29, 2026, at the age of 92.

Masterson was widely respected for his 34-year career teaching history, geography and economics at Essex District High School. Beyond the classroom, he inspired generations of students through his dedication to music and his longtime work directing the school’s choirs.

He was also a talented trumpet player who performed with several local musical organizations, including the Nil-A-Nova Band, Windsor Community Band, Chatham Community Band and the Silver Ambassadors. He regularly performed in the pit for Windsor Light Opera productions and played at numerous weddings, funerals and community events.

Masterson was a charter member of the Greater Windsor Concert Band and served as its longtime leader and musical director. Fellow musicians have remembered him as a gentleman, mentor and generous supporter who helped establish and nurture the band.

Tributes following his death have also highlighted his connection with St. Mary’s choir, where he shared his musical talent and passion for many years. Friends and colleagues have described him as a quiet philanthropist whose influence reached well beyond music and education.

Masterson was the cherished husband of the late Margaret Anne Masterson, who died in 2015. He is survived by extended family, including several nieces and nephews.

Family and friends will gather on Saturday, September 5, 2026, after 10 a.m. at Our Lady of Guadalupe Church, 834 Raymo Rd., followed by a Mass of Christian Burial at 11 a.m. Private interment will take place later at Heavenly Rest Cemetery.

In lieu of flowers, donations may be made to the Windsor Regional Hospital Foundation or a charity of choice.

The Greater Windsor Concert Band will also pay tribute to Masterson during upcoming engagements at the Quarry on Pelee Island on September 6 and RCL Branch 255 on September 27.

For those who knew Kevin, his legacy will live through the students he taught, musicians he encouraged and communities he served.

Rest in peace, Kevin Masterson. Your music, teaching and kindness will not be forgotten.