I wonder if anyone out there has ever hopped on a freight train (not as a paying passenger) the way they used to in the 1930s? Do you have any tips you could share with us, if you have? (I know it's dangerous, and illegal in most countries, but it's something I've always been tempted to try. Maybe I've read too much Jack Kerouac.)
Riding the rails, hobo style
I never tried, and I'm not sure how many open freight cars even exist nowadays, but go for it. I'd try it in America; I don't think they'll arrest you if you get caught. Americans would likely appreciate your adventurous spirit. 
Thanks for the encouragement, Eric. I got the idea a few years ago, when I was standing beside a railway track (in Canada) and a freight car, with it's door wide open, stopped right in front of me. It was almost like an invitation! I really wished I'd tried it, but I was chicken.
You're probably right, though- I think most freight cars have been replaced by containers.
Perhaps most freight cars have been replaced by containers, but not ALL of them! 
It's far better to attempt something and fail miserably at it than to wonder years from now "What if I had only dared to try?" That mindset inspired me to schedule a month-long trip to Shanghai, China earlier this week, something I had long wanted to do, though I had always found a plausible-sounding excuse not to do it (I don't have the time, it's too expensive, I can't take off an entire month off from work, etc.)
Just make contingency plans to cover everything that could happen during your trip and it'll be an amazing experience. The very fact you're daring to follow your dream makes it a trip I'd want to hear about, even if it's just an overnight trip within one province. Ever since you mentioned this idea I've been thinking about doing it myself, once I get a few other trips out of the way. It sounds like an amazing experience!
This sound so adventurous! Where are you planning to do this? Ive never thought about this before, and since I read your post I really want to give it a try. Is this really doable???
If I get back to Canada this summer, I might try this. Of course, since it's illegal, I can't go into too many details... One of the problems with hopping a freight car, is there's no schedule- you could end up anywhere.
Since I've never tried this, I was hoping somebody out there could give me a few tips (like, on how not to get killed, jumping on and off). C'mon, somebody must have tried this?
mate, your a legend!! i cant offer any advice unfortunately, ive never done it myself... just another one of those people you have inspired to give it a go... give a few months and ill have something to say about it!! 
South Americans use this method to go to Mexico and then on to the USA. (I saw a report of it on TV.) The Mexicans call the train "the monster", because every day they find a badly mangled body next to the tracks. Jumping up and down from a running train is not without risks.
I also once read a blog about it online - the writer explicitely stated that criminals on the run and mentally ill ride those trains, so you need to be prepared.
I have a few times, but only once in the "American" way - Europe doesn't have open box cars like that that you can get on. I've done it a couple of times just by talking to drivers/engineers and hitching with them, and a couple of times by hopping on to low loaders and on occassion a coal train (don't ask) when nobody was watching. Of course in some parts of the world riding on goods trains/on roofs etc is more or less normal practice, so it's not always such a big deal. I wouldn't really recomend it - these days they will likely be more paranoid about why you are doing it - but sometimes needs must
The other way, of course, is like this
poor kid although this obviously 100% illegal and also hugely dangerous [the train he is on hits almost 200mp/h, and the overhead wires offer a huge risk of electrocution]
Hello Madpoet
I never saw an open opportunity, to hop on a freight train. I dont think it is such an easy thing to do.
However, I used to hitch hike, around Europe. Is that hobo enough, for u? Although, these days that is not so easy, to do either. Truckers are no longer allowed to pick up hitch hikers. Truckers believe it or not, were the safest people, for female hitch hikers. Other people were not so safe. So hitch hiking is no longer advisable either, for women alone. 
But, if u are a guy, or a couple traveling together it would be safe enough, to do.
Mel