Series I. Early Pacific Northwest Flying contains flight schedules, clippings, flyers, expense report, poems, CLS's business card, passenger passes, map with handwritten annotation, a purchase agreement, and pilot licenses. The series largely consists of images from CLS’s time flying in the Pacific Northwest region. There are 179 black-and-white photographs and 8 photographic negatives. Lastly, the series also contains 3 videocassettes, 1 audiocassette, and 1 8mm film reel.

The documents in this series illustrate CLS's early days in the field of aviation, starting with his work with Vern Gorst’s company Pacific Air Transport in 1926. CLS was stationed in Pearson Field, Vancouver, Washington where he worked as a field attendant and aircraft mechanic. There are photographs that capture the operations of the company. Locations include Pearson Field, Vancouver, Washington, as well as Crissy Field in San Francisco, California. The Waco 9 and Ryan M-1 aircraft. CLS is featured in many images from this time period, in addition to other pilots like Henry Goode, Lonnie Brennan, Ray Small, and Russ Cunningham.

The materials follow CLS’s continued work with Gorst in Seattle, Washington and Cordova, Alaska. There are photographs of CLS and other pilots from this time period, images of then Pier 3 and Pier 5 along the Seattle waterfront where Gorst ran passenger ferries. In addition, there are materials that reflect on CLS’s employment as a pilot with the Seattle Flying Service, Gorst Air Transport's Seattle Air Ferry, and Gorst Air Transport out of Cordova, Alaska. The photographs related to this time of CLS’s career depict the locations where the commuter services ran, images of passengers as they embarked from the ferry, numerous images of the "Boeing Boat” and of Keystone–Loening Amphibians on the water, and of CLS standing with the aircraft. In addition, there are photographs of Myrtle (Smith) Scott during her flight across the Gulf of Alaska with CLS in 1930.

Following his employment with Vern Gorst, CLS became William E. Boeing’s personal pilot from 1931 to 1944. There are only a handful of records related to this part of CLS’s pilot career. Included in the file are photographs, negatives, aircraft authorization, correspondence, a flight log, and a pilot logbook.

All the files in the series are organized chronologically.