Shaila Kiley Bolger

MADISON - Shaila Ann Bolger, age 92, passed away peacefully on Wednesday, April 2, 2026, surrounded by love.  She was born in Milwaukee, Wis., on December 1, 1933.

Shaila had a deep love for nature and animals, and she shared that appreciation with her children-shaping who they became and inspiring their own love of the natural world. From a young age, Shaila was drawn to horses, a passion she carried throughout her life. She was a skilled dressage rider-often described as “ballet on horseback”-and competed successfully at advanced levels.

Shaila attended Northwestern University, where she pledged Kappa Kappa Gamma. However, it was years earlier, as a freshman at University School of Milwaukee, that she went on her first date with her future husband, Tom. At the time, she could not have known that the two would share a love story spanning more than 70 years of marriage. Partners in every sense, they complemented one another and felt deeply grateful to have found each other. Their life together was rich with close friends and family, and they were fortunate to travel the world with many of them. They always returned home to their lives in Madison and Fox Run Farm in Richland Center. “The Farm” was a special place that fed their souls and enriched their lives beyond measure. It was there that large groups of family and friends gathered, laughter rang out, and where they also found quiet peace in the evening song of a whippoorwill, a deep snowfall, or beneath a night sky.

Shaila was a devoted and steadfast friend, the kind of person who showed up without being asked and stayed as long as she was needed. Loyal to the core, her friendships were enduring and deeply rooted in trust and kindness. She also carried an easy sense of humor -quick to laugh, often at herself.  Her generosity flowed naturally; she gave her time, her attention, and her care freely, never keeping score, and always finding simple, meaningful ways to lift others up. Finally, and most important, Shaila’s (Nonnie to her grandchildren) greatest joy was her family. Her love for her children and grandchildren was boundless-an enduring presence of guidance, encouragement, and warmth.

Shaila is survived by her devoted husband of 70 years, Thomas E. “Tom” Bolger; their four children, Tisha (Debra), T.J. (Mary), Ann Munsey (Mike) and Jim (Blaine); grandchildren, Walker (Maggie), Kiley, Parker (Josephine), Sawyer, Shaila, Zoe, Finn and Daisy; many loving nieces and nephews; and dear friends, Gloria and Linda. She was preceded in death by her parents, Olive Herzfeld and William (Bill) Kiley; her beloved stepfather, John Herzfeld; and siblings and their spouses, Bill Kiley (Essie), Tim Kiley and Mary “Cissie” King (Paul); and by several loved horses, dogs and two cats, Scaredy-cat and Tom-cat.

The family wishes to express their profound and heartfelt gratitude for the exceptional, compassionate care Shaila received from the staff at The Haven at Attic Angel Community and Agrace Hospice.  Their kindness, attentiveness, and unwavering dedication ensured that Shaila was surrounded by comfort, dignity, and respect in her final chapter. The tenderness they showed-not only to Shaila, but to all who loved her-will never be forgotten.

The immediate family will hold a private celebration of Shaila’s life this summer in Montana.

Online condolences may be made at www.gundersonfh.com.

Gunderson West

Funeral & Cremation Care

7435 University Ave.

(608) 831-6761