Wendy Lee Calise

On October 24th, 2025, Wendy Calise, aged 59, passed away peacefully, surrounded by her beloved family at home. Wendy is survived by her three children (Dante 27, Cecilia 23, Rino 20) and her soulmate and husband of 36 years, Guy.

Wendy impacted countless lives during her time as a teacher at Countryside Day School (formerly Countryside Montessori), eventually taking on the role of head of school, where she strengthened the incredible community her parents, the founders of CDS, dedicated their lives to cultivating. Wendy was a deeply loved and highly renowned figure in the Montessori community, across the country and around the world.

When Wendy was diagnosed with primary breast cancer for the first time 18 years ago, she was fearless and unwavering, not allowing the diagnosis to hinder her mission as an educator in the slightest. A second diagnosis of recurrent metastatic cancer came ten years later, with a prognosis of 3 to 5 years at the time. That was now eight years ago. She feared she would not live to see her youngest child finish high school, but even she had underestimated her own strength. Wendy continued dedicating herself to her work at CDS, silently carrying the weight of a terminal diagnosis while unwaveringly leading a school, community, and family.

In the last decade, Wendy endured more suffering and loss than most people will in a lifetime. The five years following her second diagnosis, she lost her sister Krista, her mother Annette, and her Father Frank, and Wendy cared for each of them right to the end, all while carrying the weight of her own prognosis.

In the past two years, Wendy's cancer began to worsen more rapidly, and while treatment slowed its progression, the mental and physical toll continued to grow. Nonetheless, she maintained her spirit, strength, and resilience through every step, undergoing many treatments and surgeries with the hope of improvement. When she had finally given the last of the strength she had to give, she made the courageous decision to enter hospice care and spend her final moments with the ones she loved while she could still be present.

Wendy was a compass to so many people she touched, providing wisdom and guidance in all areas of her life. Most of all to her family, she was our guiding light. She was at each of our sides through the good, the bad, and the ugly, all the while shouldering the weight of her own personal loss—a weight most could not endure.

Many in her situation might have felt angry or shortchanged, but Wendy never asked, "why me?" Through it all, she maintained the selflessness, bravery, humor, and gratitude that made her the extraordinary woman she was.

Wendy was an inspiration in a way that only those who knew her can understand, and she will be missed by those who love her more than words can describe. Our wish is that everyone she has touched over the course of her incredible life remembers her for the woman she was and for the gifts she leaves behind. In her final days, Wendy conveyed to us, her family, not sadness or anger but rather gratitude; gratitude for the life she got to live—the life she built.

In lieu of flowers, we ask that you please share by email (g3calise@gmail.com) any fond memories or photos you may have of Wendy. We believe that sharing memories and remembering the incredible woman she was is the best way to honor her now.

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