The Family

Sweet Grass is a family-owned and operated guest ranch that recently celebrated our 61st anniversary. Bill and Shelly Carroccia and their children, Page, Rocco, and Tony, live and work near the guest ranch or cattle ranch, helping with all aspects of operations. Their oldest son, J, lives with his wife in California, but visits often. Bill and Shelly’s fourteen grandchildren are the sixth generation to grow up in the mountains of Montana, and have spent all the summers of their young lives working at Sweet Grass.

Bill and Shelly

Shelly Van Cleve Carroccia grew up on her family’s guest and cattle ranches in Montana, where the Van Cleve family homesteaded in the 1880s. Shelly’s grandpa, Paul Van Cleve, was one of the founding directors of the Dude Ranchers’ Association in 1926, so dude ranching is in our blood. Paul bought Sweet Grass Ranch from the Brannin Family, who homesteaded here in the late 1800s. In 1963, Shelly married Bill Carroccia. In 1965, they bought Sweet Grass from her grandpa. For the first few years, Shelly and Bill ran Sweet Grass as a kids’ camp. In the ’70s, they switched to taking families. Bill and Shelly worked as school teachers and cattle ranchers for decades, putting everything back into Sweet Grass. They built the ranch into what it is today – the epicenter of our family, and a place that feels like home for the thousands of people who have visited us over the last sixty-one years.

Page & Pat – and their kids Erin & Connor

Page, her husband Pat, and their two children, Erin and Connor, live at Sweet Grass during the guest season. Page is our boss lady, overseeing all aspects of the business from paperwork and bookings to managing the kitchen — all while continuing her legal practice and serving as the city planner.

Pat balances his role as the Sweet Grass County Attorney with hands-on involvement at the ranch. From leading building projects, managing handy-men, grilling steaks and spraying weeds, Pat truly does it all.

Erin and Connor manage the daily operations of the ranch, including guest and employee scheduling, the corrals and horse care, hiring wranglers, and more. Erin’s fiance, Wynne, is also on the ranch, lending a helping hand with maintenance projects and shoeing our ponies.

Rocco & Annie – and their kids Rainy, Lily, & Ryal

Rocco, his wife Annie, and their kids, Rainy, Lily, and Ryal, run our family’s historic cattle ranch, Otter Creek Ranch. Rainy, Lily, and Ryal are frequently at Sweet Grass during the summer, helping out in the corrals, kitchen, cleaning or wherever else we need a hand. Rocco and Annie run the main group of our Sweet Grass horses on the cattle ranch during the winter, keeping an eye on the horses as they run wild through thousands of untamed acres.

Tony & Laura – and their kids Orry, Zandy, Juliet, & Jack

Tony, his wife Laura, and their children, Juliet and Jack, live in Melville. Tony’s twins, Orry and Zandy, live in Boise and Bozeman, respectively, but frequently visit the ranch on weekends. Tony is a teacher at the three-room rural school in Melville, where most of our family was educated from kindergarten through eighth grade. He also fixes small engines at his machine shop in Melville. Laura serves as the clerk for the rural schools in Sweet Grass County.

The family spends much of their summer at Sweet Grass, with Tony often providing musical entertainment during the evenings. He and Laura contribute to projects around the ranch, while Jack and Juliet are learning to love riding (or dirt bikes).

J & Annette – and their kids Kris, Josh, Rouaine, & Gio

J and his wife, Annette, live in Twenty-Nine Palms, California. J served 23 years with the Marines before retiring and becoming a civilian contractor. Annette manages a movie theater on the base. They visit the ranch as often as possible!

Their oldest son, Kris, resides in Spokane with his wife, Stefani, and their children, Julian and Abby. Kris serves in the Air Force, balancing his career with family life. Stefani is a nurse, and Julian spent his first season working at Sweet Grass in 2026 – making him the first of Bill and Shelly’s great-grandkids to carry on the tradition!

Josh works remotely for a tech company and spends summers at Sweet Grass, where he is our part-time chef and full time fixer of all things, ranging from plumbing projects to building bar trailers to our very own tech support. Gio, who has worked as a wrangler during past summers, is currently pursuing his Master’s degree in Bozeman but visits the ranch whenever possible. Rouaine lives in Twenty-Nine Palms with her husband, Oscar, and their three children—Jacob, Noah, and Sophia.