Raymond Paul Rugg, Jr.– Ray– packed his first hunting party into the hills by himself in 1956. The several-days-late arrival of a party after Grandpa and all of the other guides were in the backcountry to pack game out from the base camp required the 12–year–old Ray to guide the latecomers into camp by himself.

For nearly the next two decades, Ray worked on–and–off again as a professional guide. When he returned from military service in 1970, he guided for Gulli at the Hole–in–the–Wall, until Tony sold the lodge in 1973. By the spring of 1975, Ray had had so many hunters requesting that he guide them that he finally took his outfitter's exam in 1975 and began outfitting and guiding in Montana again. In 1978, he decided to expand his operations, and bought out an outfitting unit in Idaho's Selway-Bitterroot area. From that time up until 1995, Ray outfitted in both Montana and Idaho.

In 1994, Ray sold his ranch in the Mission Valley of Montana and moved to Superior, on the Clark Fork, in order to be closer to the outfitting areas. In 1995, he sold the Selway outfitting, and in 1996, took advantage of the opportunity to expand both his Montana summer schedule and to acquire a closer unit in Idaho, so he bought out Great Northern Outfitters and combined those operations with his existing Rugg's Outfitting business.

While all of Ray's four sons have helped out with the outfitting business in various capacities throughout the years, youngest son Kip passed his outfitter exams in 2007 and has taken over the Superior Ranger District operations, along with the River operations. Ray still heads up the outfitting operations in the Nine Mile Ranger District and the St. Joe Ranger District in Idaho, while son Korey, a wastewater operator for the city of Missoula pitches in whenever he can.