Wee, at 6:30 Tues. morning May 14th, 1901, a freight came puffing in to the little station of Oregon City, Ore. We, John, Tom & I were standing about the depot watching the train, of course. Well, we spied an empty boxcar & in we went. The train had hardly stopped when the brakeman came around with some freight for the very car in which we had hid. In loading the car they happened to spy us and said unload boys, come unload & of course we unloaded. Well, what would we do dumped at the very beginning of our cruise? We tripped on up the track a ways, determined to ride just the same. The brakeman, a pleasent looking young man came along again & said “Boys, where are you going?” We said Calif. & he said “Gee Whiz”, a long way to bum, got any chink?” We said a little. Well, he says, give me 50¢ apiece & I will carry you to Junction City – 88 miles from Oregon City. Well, of course, we gave him the 4 bits. There was only one place to ride & that was under a lot of wheels (carwheels) on a flat car just behind the engine. A dirty place to ride, I tell you. Anyway, we rode the car of car wheels for about 60 miles then they took on a car of lumber, in which we rode the rest of the way. We got to Junction City about 5:30 but was truly ashamed to approach civilization for three blacker persons you never saw. Wood, dust & cinders an inch thick, more or less. Between Ore. City & Junction City we helped load the engine a couple of times with wood, for they burn wood on the S.P. RR. [Southern Pacific Railroad] When we got to Junction City we went to the hotel & washed the dirt off & ate supper. At about 7:00 another freight pulled out of Junction City & on it, of course, we were. No place to ride only on a flat car under a separator – – a cold place to ride indeed. In about an hour the brakeman came around (a different one) & asked us where we were going & if we had any money & we gave him a dollar. Well, we rode for about an hour when along came the conductor & said “tumble off, Bill & help load up the wood”. We boys stood the cold on the flat car under the separator till morning by bless you, I like to froze & when the train stopped I went back to the engine that was pushing us up a 9 mile grade & said to the engineer, “let me pass wood on the engine” & he said “I dont care”. So I passed wood on the engine till we reached Roseburg about 100 miles from Junction City.
Fifty cents in 1901 has the same spending power as $15.03 in 2019. One dollar is double that, $30.06.
Vox has a great article on all the ways that hobos travels on trains, although it does not mention the bartering and helping to pass wood up front.