The only caboose ride I've ever taken was on the Cumbres & Toltec and it was obviously not a long distance nor was it a revenue run....on the other hand I do have some information about others who have ridden a caboose in revenue service...
"On the Pere Marquette, a train of empty freight cars was rumbling out of the yards at Benton Harbor, Michigan. Back in No. A616, Conductor Roy Blodgett called over to his rear brakeman, Charlie Webster: "A bird is chasing us." When the train stopped, the trainmen discovered that a mother robin had built her nest on the under side of the crummy. In it were three blue eggs. Ward Salsbury, head brakeman saw the men peering under the caboose and he yelled: Whatsa matter; got a hot box down there?"
"No," the conductor shouted back. "A robin's nest. Go easy will you?"
So Engineer Charlie Wilcox did his darnedest to make the starts and stops as joltless as possible all the way to Hartford, Michigan. The fireman was Howard Peck. On the return trip to Benton Harbor, the caboose was placed exactly in the same spot on the storage track from which it had been taken, in the hope that Mrs. Redbreast would go back to her eggs. Sure enough, she did.
The story spread, arousing sympathetic interest. C.A. Wilkins, general agent and former train dispatcher, decided that something should be done about it. He telegraphed J.G. Grigware, superintendent of the Chicago-Petoskey Division at Grand Rapids, explaining the situation. Back came the order:
"Use extra caboose until robin is done with car"
Mr. Grigware sent an extra crummy to Benton Harbor.
From A Treasury of Railroad Folklore - Botkin and Harlow
