June 25, 1941: "Fly lake, a new position this year, with a tower built in a tree and tent for living quarters at the foot of the tree, patrolled by Allen Madsen of Camp Sherman." (The Bend Bulletin)
July 1941: The 75-foot tree lookout was located at the site of the Guard Cabin. The tower that was constructed in 1948 was located several hundred yards to the east of the guard cabin.
August 13,1941: Allen Madsen was transferred to the Black Butte lookout in mid-August. (The Bend Bulletin)
1946: Paul Striebel was the fireman stationed at Fly Lake. The lookout at this time was in the top of a 73-foot tree.
August 25, 1948: "On the Sisters district, a new lookout tower has been erected near Fly lake. This tower is 53 feet high, and its first lookout was Paul Streibel." (The Bend Bulletin)
1953: A plan T-1E wood frame 16x18 garage was moved to the lookout from another site.
June 17, 1953: "Mr. and Mrs. Joseph Burns now are on duty at the Fly Lake Lookout station." (The Bend Bulletin)
1956: "Lines are still maintained to the USFS lookout at Fly Lake and to the State lookout on Hinkle Butte. The telephone line to Fly Lake Lookout has been maintained by the State for a number of years in exchange for lookout coverage in the northeast area of the Sisters Unit. There is no contemplation of doing away with these lines. Maintenance is usually fairly light. 1956, however, was a rough year for maintenance as considerable logging and county road construction occurred that necessitated moving the line to Fly Lake several times." (Central Oregon District Annual Report)
June 8, 1962: "A lookout to be placed on the Fly Lake lookout of the Squaw Ridge area." (The Bend Bulletin)
1965: David Snow was the lookout-fireman. This was the last year the lookout was staffed.
April 17, 1968: "The Oregon State Highway Department has a construction contract for five miles of road to Fly Lake Lookout. The remaining four miles is under U.S. Forest Service contract and begins at the Lookout. This road is not recommended for house trailers." (The Oregonian)