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Single, Looking to Hook Up: 1943

Chicago, April 1943. "General view of part of the South Water street freight depot of the Illinois Central Railroad. Chesapeake & Ohio R.R. caboose." 4x5 Kodachrome transparency by Jack Delano for the OWI. View full size.

Chicago, April 1943. "General view of part of the South Water street freight depot of the Illinois Central Railroad. Chesapeake & Ohio R.R. caboose." 4x5 Kodachrome transparency by Jack Delano for the OWI. View full size.


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The "Moose Caboose" in Kennett, MO

There used to be a train with a caboose that came past our small cotton farm in Kennett, MO and we would wave to the engineer if we were out in the pasture area of our place... We also would always wave to the guy that was always back in the caboose area of that small train... The engineer always tooted his whistle at us to let us know that he had saw us and that made us happy that "The Moose" had said "Hello" to us 8-)

The railroad tracks and the train no longer runs in Kennett and our small cotton farm is no longer there either, as small town suburbia has taken over most of the small farm land(s) that is/were on City Limits. It is always sad to go back to our hometown and see that lonely, empty weedy abandoned railroad track... 8-(

Ruth Chambers Holt (aka --> TheSteelButterfly)

Caboose Driver

My grandfather was a caboose driver in Ohio in the Forties and Fifties. On certain days his kids used to gather at a certain part of the track after school and he used to throw them the leftovers from his lunch. Unfortunately I never met him because he died before I was born.

Well, Steve Goodman anyway.

Steve Goodman was the writer of the song. Arlo has a pretty neat story about how he met Steve and the song.

Arlo Guthrie on the Illinois Central

Illinois Central Monday morning rail
Fifteen cars and fifteen restless riders,
Three conductors and twenty-five sacks of mail.

Waving remembered

Yes, I also remember how the guys in the caboose (and the engine, too!) would return our waves. What was it about railroaders that made them so friendly to kids? Today, nobody has time for that. We as a society have lost so much in the last 70 years!


Like HME, I'm old enough to remember us kids on the playground, next to freight tracks, waiting to wave at the guy in the caboose, who always waved back.

Loose Caboose

Some railroads around the Chicago area still use a caboose for switching because of the necessity to run with the engine pushing the train. Also it offers more protection while preforming the switching operation and to allow the brakeman to be closer to the needed cars. The South Shore Line still uses a caboose and before the Union Pacific bought The Chicago and Northwestern many local or switching runs used a caboose. the later were in bad shape, very rusty and most if not all the windows had been covered with steel.

Little Red Caboose

As a very young kid, possibly 5 or 6, we used to sing, upon seeing one of these:

Little red caboose, chug, chug, chug,
Little red caboose,
Little red caboose behind the train, train, train, train,
Smokestack on its back, back, back, back,
Coming down the track, track, track, track,
Little red caboose behind the train.

Now I will take my pills and go to bed.

Hibbard, Spencer, Bartlett & Co.

Since no one else seemed to mention it I guess I'll throw it in. Although the building no longer exists, HS&B carries on under the familiar name of True Value Hardware.

I still see cabooses

I still occasionally see cabooses up here in Canada. The CN uses them on short local switching runs out in the area, presumably because it would be too much of a hassle to disconnect and reconnect the FRED every time they dropped and added a new car. I've always wondered about the ride in a caboose.

Cupolas for Dummies

The cupola provided a lookout. Where you see the windows on the outside of the cupola, you'll find seats (not comfortable) on the inside.

A crewman, usually the rear brakeman or flagman, would occupy a seat, facing forward so he could watch the train ahead for any problems such as a dragging load, or a "hotbox" (an overheated friction bearing journal that could cause a serious derailment). There was also an air gauge and an emergency air valve so that the train could be stopped if needed by bleeding off the train airbrakes from the caboose.

As freight cars grew larger, the cupola became less effective. There were also safety issues, as crewman could and did fall out of the cupola, a drop of several feet. Some roads opted for bay window cars as a result.

That toddling town

The gothic tower in the foreground is the Tribune Tower at 36 stories. The more distant one is the InterContinental Hotel, 42 stories. If wikipedia is to be believed, the mast on the hotel was built so that dirigibles could dock there.

I Have a Dream

I always dreamed of having a caboose like this sitting on a piece of property somewhere - just outfitted enough to be an escape from the daily grind. It is never going to happen, but it is a nice dream.

The End

I remember when I was little trains still had cabooses, and all the kids would be excited to wait for it at the end as the man would always wave and smile at us. I think I was only about 7 or 8 when most of the railroads decided to switch to automated cameras instead, but I remember being quite sad about it.

Purpose of the cupola

You can read about the cupola on wikipedia (lots of other good info on cabooses (cabeese?) too).

Re: Skyscrapers

The building behind the Tribune Tower is the old Medinah Athletic Club. It's now the Intercontinental Hotel, and still has the beautiful ceramic-tiled indoor pool from the athletic club days. The distant building just to the right of the caboose is probably the old Allerton Hotel (home of the Tip Top Tap) on north Michigan Avenue, also fully remodeled in the last few years. Love those Jack Delano railroad pics!


Yay, Jack is back! To the left, with the flag atop it, is the Tribune Tower, looking rather soot-stained. To the right, with the copper dome, is the former Medinah Athletic Club, now known as the Hotel Intercontinental.

I See What You Saw

The cupola was used by the rear end crew (Conductor and Brakeman) to watch the train in front of them. They had the responsibility to watch for smoking/burning axle journals, broken and dragging equipment, derailments, and the train uncoupling. It's an interesting view of the railroad, I have ridden in the caboose train at the Illinois Railway Museum in Union several times. Incidentally, the caboose rode on special trucks that gave a slightly smoother ride than a regular freight car.

The tall building closest to the camera is the Chicago Tribune. I do not know the name of the building with the onion domed top. -- Ken

Cupolas and Skyscrapers

1) The cupola was there so crew could sit on elevated seats and look out over the train to see if there were any problems.

2) The Wrigley Building.


Main reason was so those in the caboose (conductors, brakemen, guards, etc.) could get a better view of the forward part of the train to ensure nobody was riding the roofs, that they were still attached to the engine, and other potential threats.

That Tall Building

I believe that would be the Chicago Tribune in the background.

The Cupola

In the days before sophisticated trackside detection equipment, and F.R.E.D. (flashing rear end detection device), the condition of the cars in a moving train was determined by three of our five senses. The head-end brakeman in the locomotive and the conductor and rear-end brakeman in the caboose were required to look, listen and smell for signs of hot wheel bearings, loose loads, dragging brake equipment, etc. Myth has it that the first cupola was invented near the scene of this picture when a mid-nineteenth century conductor stuck his head through a hole in the roof of a derelict boxcar being used as a caboose and was amazed at the better view it gave him of the train. Chairs on the roof and eventually a small shelter quickly followed. Some railroads, for clearance and other reasons, favored a "bay-window" on either side of the caboose. The Pennsylvania (The Standard of The World) and several other railroads put rear-facing "doghouses" on locomotive tenders as kind of a cupola for head-end "brakie."

Cupolas and Skyscrapers

What was the cupola on a caboose for? and what's that tallest building the background, please?

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