I think your best bet to gettin on a train and meeting that desire to feel that wind against your face would be to show up to some anarchist/punk events and ask around, see if you can meet someone there who knows their way around trains and can get ya your greenhorns. It is very dangerous and also, I think you are capable of meeting that danger if you take some patience and care into your preparation for the trip. Finding someone who knows the inner workings of train hopping will be your safest bet for a smooth ride,
don't go alone, or with someone inexperienced. I get that's kinda hard to socialize and put urself out there sometimes tho, I mean it's hard for me to do! But don't be discouraged.
A quick search found this group in NYC
https://www.instagram.com/iohnyc/?hl=en looks like they do mutual aid and distribute food and other things, i bet you could meet someone here who knows trains, or someone who may be able to point you in the right direction to start familiarizing yourself with the terrain.
Anyways, best of luck retrobarbie, stay safe stay dangerous ^^