95th annual Pioneer Day Queen Lorraine Jespersen Cagliero
By Camille DeVaul · Fri Oct 10 2025
This year, Lorraine Jespersen Cagliero takes center stage as Paso Robles Pioneer Day’s 95th Queen, carrying forward a legacy that stretches back to the late 1800s. Her story is one of ranching roots, civic service, and a deep love for family and community.
When Lorraine learned of her new royal title, she told Paso Magazine, "I was overwhelmed. There’s so many people [who deserve this].”
Lorraine was born in 1943 on the Kentucky Ranch west of Templeton, now known as Thatcher Winery. Her ancestry is steeped in Paso Robles pioneer history. Her great-grandfather, Christen Iversen, immigrated from Denmark in 1882 and homesteaded 160 acres in the Union District. From there, the family’s journey took them along the Estrella River on Shandon Highway, where they ran a thriving feed yard with 200 horses and eventually landed near San Miguel.
Lorraine, proud of her family’s steadfast dedication to agriculture, shared, “For generations our family has been in farming.”
Christen later married Anna Christensen, and together they had Lorraine’s grandmother, Jennie Iversen, who would go on to marry Chris Jespersen. Chris’s family also traced its roots to Denmark; he was a descendant of Christen Jespersen, an immigrant who homesteaded in the Union District in 1863. In 1965, Jennie served as the Pioneer Day Queen.
Chris Jespersen went on to serve as a state assemblyman and then as state senator for
San Luis Obispo County, leaving a lasting mark on the community by helping secure property for Camp Roberts, Paso Robles Boys School, Atascadero State Hospital, Camp San Luis, and the Paso Robles Airport. Senator Jespersen also fought to preserve California State Polytechnic (Cal Poly), ensuring the university’s growth into the institution it is today, and championed a school for children with cerebral palsy, which now bears his name.
Lorraine’s father, Lawrence Jespersen, was born in 1915 as the eldest of Chris and Jennie Iversen Jespersen’s five children. He graduated from Paso Robles High School and later earned a degree in Poultry Science from Cal Poly. In 1941, he married Ruby Lapp Luther, a fellow descendant of pioneering families in the area and the 1940 Pioneer Day Parade Belle. Ruby, born in Templeton in 1922, had been a 4-H all-star, attended Oakdale School, and graduated from Templeton High School. Together, Lawrence and Ruby, along with the Jespersen family, established the Kentucky Ranch in Templeton in 1943.
In 1945, the family moved to Los Osos, where they operated a grade B dairy, and Lorraine attended the one-room Los Osos Valley School with just 16 students until the fourth grade. The Jespersens returned to Paso Robles in 1954, purchasing a ranch on North River Road to farm alfalfa hay and sugar beets—the very land where Lorraine’s son Jon and his wife now farm wine grapes and pistachios. Lorraine continued her education at San Miguel Grammar School and graduated from Paso Robles High School in 1961, serving as a student body officer for three years and participating in the American Legion Auxiliary California leadership program, Girls State.
“We think we grew up in the best time. Nobody worried about designer clothes ... everybody was just hard working ... and it was a good life,” Lorraine says, looking back fondly on her childhood.
High school also brought young love. Pete Cagliero, her neighbor, would become her husband, business partner, and lifelong companion. Together, they farmed the North River Road Ranch and eventually acquired the Jespersen Ranch, expanding their operations to include cattle, hay, grapes, and pistachios. They raised three children—Dena, Jon, and Phillip—instilling in them the same values of hard work, family, and community that defined Lorraine’s own upbringing.
Beyond the ranch, Lorraine has been a pillar of her community. She has served on the boards of the Cuesta College Foundation and French Hospital Medical Center Foundation, contributed to the El Paso de Robles Area Historical Society, and supported Mission San Miguel projects. Her dedication to agriculture and ranching was recognized in 2015 when she was named Cattle Woman of the Year.
Even after Pete’s passing in 2004, Lorraine has maintained a vibrant life, balancing travel, entertaining, and ongoing community involvement. Yet, her greatest treasures remain her family—five grandchildren and two great-grandchildren—and the enduring connections to the Paso Robles community that have defined her life.
As the 95th Pioneer Day Queen, Lorraine Jespersen Cagliero embodies the heart of Paso Robles: a love for family, a devotion to community, and a deep respect for the pioneers who came before. Her story is a living bridge between the past and the present, reminding us that the spirit of Paso Robles is carried not just in its land, but in its people.
You can learn more about the Pioneer Day Royalty at pasoroblespioneerday.org/royalty
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