Richard Len Hiles was born on June 6, 1934 to Milton and Hilda (Galbreath) Hiles in Beadle County, White Side Township, South Dakota. He and his family moved to Black Hawk, South Dakota when he was two weeks old until 1946. Growing up in the Black Hills, Rich and his brothers had many adventures; from riding ponies, catching rattlesnakes and playing with guns. His family moved back to Broadland where he attended country school. He helped his father farm until the age of 14. He started trucking with Leroy Newman.

Richard married Elizabeth Boomsma in 1951 and to this union four children were born; Robert, Julie, Russell, and Tony. In 1962, Rich started his own trucking company. Along with his trucking company he started Hiles farm in 1964. With the help of his sons, his fleet grew to a number of his custom green cabovers.

Richard met Peggy Hopper in 1985, they were married in 1998 and to this union, one daughter was born, Caycee. Rich also gained two step-children, Tony and Laura.

With the help of his sons, grandsons, and great-grandsons the family farm grew into what it is today. He loved his family and friends and spending time with them was important to him. Rich went to breakfast at Bales every morning since the café opened many years ago. He looked forward to camping, especially at Wheel Jam where he was awarded the 1st lifetime achievement award. He was an icon in the trucking industry and everyone knew those green Kenworths. His passion for trucking kept him trucking until the day of his passing.

He is survived by his wife Peggy of Huron; children Russell Hiles and Tony (Kris) Hiles both of Wolsey; 2 daughters Julie (Kevin) Willis of Shelton, NE and Caycee (Jerad) Carlson of Kadoka, SD. Stepson Tony (Pam) Beerman of Huron and stepdaughter Laura (Scott) Jones of Huron. Fourteen cherished grandchildren; Michelle (Paul) Johnson, Kris (Troy) Brandt, Scott (Kari) Willis, Marc (Melissa) Willis, David (Lindsey) Willis, Brandy (Jeremy) Timm, Eric (Ashley) Hiles, Michael (Stacy) Hiles, Jade (Stephanie) Weideman, Tessa Weideman, TJ (Misty) Weideman, Chisum (Mandy) Hofer, Madisen Larsen, and Ava Beerman; and 30 great-grandchildren. His sister Mary Alice Ferguson of Salt Lake City, UT, daughter-in-law Carolyn Hiles of Wolsey, mother-in-law Ursula Hopper of Huron, siblings-in-law Cheri (Terry) Ritchhart of Cheyenne, WY, Jeff (Louisa) Hopper of Huron, Brad (Lisa) Hopper of Sioux Falls, Pami (Jeff) Osborne of Peoria, AZ, and Kathleen Wachter of Lake Shasta, CA. Rich also leaves behind his beloved dog, Bentlee.

Rich was preceded in death by his son Robert in 2015; his parents Milton and Hilda; and his brothers, Mel, Wilford, and Delbert.