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The Classic Caboose: An American Legend
Perhaps no other symbol of American railroading has defined the industry as the simple caboose. An endearing piece of equipment, even to the general public, the car was an all too common sight that many folks anticipated watching pass as the end of the train went by. First reportedly developed just a few decades after the Baltimore & Ohio Railroad was chartered the caboose became a vital part of a freight train for over a century with several different types and versions of the car developed during that time mostly in regards to how a particular railroad designed their particular type for everyday use (such as the Pennsylvania, Reading, B&O, and others). While still in limited use today the beloved caboose has mostly went extinct as it rapidly disappeared beginning in the 1980s.
https://www.up.com/aboutup/history/caboose/early_uses/index.htm
The origins of the railroad caboose appear to date back to the 1840s when Nat Williams, a conductor of the Auburn & Syracuse Railroad (a later affiliate of the New York Central) became fed up with cramped and uncomfortable quarters to do paperwork (a common job of the conductor, whose responsibility is general oversight and control of a train, passenger or freight), which was usually done in either a free space of a passenger car or combine/baggage car. To fix this problem, Williams found an unused boxcar and using a simple box and barrel, as a seat and desk, set up shop in the car to do his duties. Not only did he find out he had plenty of room to work but also figured that he could use the unused space to store tools (flags, lanterns, spare parts, etc.) and other essentials to have on board whenever needed (such things become commonly stored on the caboose).
Since non-locomotive personnel on freight trains did not have assigned quarters (space in the locomotive in those days was at a premium unlike today) so the “conductor’s car,” as it was originally called, quickly caught on across the industry. At some point, and it is not known exactly when, the term caboose began to be applied as the car’s name. In any event, at first these cars looked like short, stubby boxcars (or were boxcars) called bobbers, with just two axles and no truck assembly. Eventually, however, railroads began to understand the car’s potential and through the years upgrades and additions began to appear.
Perhaps the most striking feature ever applied to the railroad caboose was its cupola. According to the story, conductor T.B. Watson of the Chicago & North Western in the 1860s reportedly used a hole in a boxcar’s roof (which he was using as a caboose) to get a better vantage point of the train ahead. It is said that Watson was amazed by the view afforded from the position being able to not only see the train ahead but also from all sides, and to the rear as well. He apparently convinced C&NW shop forces to construct a type of open observation box onto an existing singe-level caboose with windows all around where one could sit and view their surroundings. The rest, as they say, is history and the common cupola was born. More here https://www.american-rails.com/caboose.html#gallery[pageGallery]/0/
Caboose Types:
original uploader was Slambo at English Wikipedia
Cupola or "standard"
The most common caboose form in American railroad practice has a small windowed projection on the roof, called the cupola. The crew sat in elevated seats to inspect the train from this perch.
The invention of the cupola caboose is generally attributed to T. B. Watson, a freight conductor on the Chicago and North Western Railway.
original uploader was Slambo at English Wikipedia
Bay window
In a bay window caboose, the crew monitoring the train sits in the middle of the car in a section of wall that projects from the side of the caboose. The windows set into these extended walls resemble architectural bay windows, so the caboose type is called a bay window caboose. This type afforded a better view of the side of the train and eliminated the falling hazard of the cupola.[citation needed] It is thought to have first been used on the Akron, Canton and Youngstown Railroad in 1923, but is particularly associated with the Baltimore and Ohio Railroad, which built all of its cabooses in this design starting from an experimental model in 1930. The bay window gained favor with many railroads because it eliminated the need for additional clearances in tunnels and overpasses.
Extended-vision
In the extended-vision or wide-vision caboose, the sides of the cupola project beyond the side of the car body. Rock Island created some of these by rebuilding some standard cupola cabooses with windowed extensions applied to the sides of the cupola itself, but by far, the greatest number have the entire cupola compartment enlarged. This model was introduced by the International Car Company and saw service on most U.S. railroads. The expanded cupola allowed the crew to see past the top of the taller cars that began to appear after World War II, and also increased the roominess of the cupola area. Source Wikipedia Caboose types