05/11/2026
This month’s featured Rubicon Trail Adventures trail guide is Chipper Ross! We have often said that Chipper was “born on the trail,” but little did we know how accurate this was! Chipper is part of a multi-generational Jeeping family who were very much a part of the Rubicon Trail’s legacy.
Chipper’s grandparents brought his Mom home from the hospital in a 1945 Willys MB. Six months later they took that baby on her first wheeling trip in that Jeep while she was cradled in a pillow lined laundry basket! That little MB completed ten Jeepers Jamborees from 1954 to 1964, thus paving the next generation of Ross Jeepers!
In 1969, Chipper’s parents bought a 1946 CJ2A. The Ross family vacations brought them to The Rubicon Trail, Sierra Trek, and the Calistoga Jeep trails starting when Chipper was just 6-months old. It’s no wonder his first words were not “Mama” or “Papa.” Of course, baby Chipper’s first word was “Jeep!”
Chipper’s dad later opened a shop in Half Moon Bay called Scottie’s 4WD, while his mom worked for Specialty Jeep Parts in South San Francisco. Immersed in the Jeep culture, 9-year-old Chipper was allowed to drive the CJ2A in low range first gear in the field around their house…Which resulted in a rather humorous situation when a CHP officer pulled him over one day!
By 12-years old, Chipper and a friend successfully drove the Jeep over the trail from Loon Lake to Rubicon Springs. Talk about learning how to choose your lines early!
As you can see, Chipper brings some amazing history and trail knowledge to Rubicon Trail Adventures. He knows every inch of the Rubicon Trail, and as a result, he does a fantastic job spotting our customers over every obstacle with finesse!
Chipper and his wife reside in El Dorado County. They have a wonderful daughter who is in fifth grade and two sons, both of whom proudly serve in the U.S. Navy!