In urban exploration, no matter what kind of, you do trespass, sometimes not even knowing that you trespass. And once in a while you are caught. How bad it is? A wonderful guide for rooftopping in particular I found here: https://www.reddit.com/r/urbanexploration/comments/2twini/ It is a very good and useful instruction in general, (especially section 3 “Getting up to the roof”, perfectly written as something to refer to). As for trespassing, and what charges apply, proceed to section 4, “Getting Caught”. It is, of course, nothing nice. The advices he gives are not particularly for rooftopping, they are basically for any sort of UE. I would add that, first of all, you should dress nicely. To a person who is good dressed, the attitude is very different (read the comment in the middle, from major_t0m). Then, do it on the night from Saturday to Sunday. It is the best time, ever. Some trespassers were, indeed, arrested in Toronto recently, however on practice it is very rare that you deal with law afterwards, it is even very rare that you get caught at all (that’s why those guys made big news; if it was common, they wouldn’t: ). Just keep these things in mind: if you are caught, be polite, explain the situation, they will likely be too lazy to bother with you and you will be excursed from the building. An article was published in The Guardian (www.theguardian.com/cities/2015/feb/17/rooftoppers-urban-explorers-risk-photographs-skyscrapers-bradley-garrett ) which also mentions some arrest. Yes, it happens, but does it make sense to always be afraid? Then we would all just be sitting at home all the time impassable. Life outside of comfort zone is dangerous, but why not just being careful and planning everything in advance? As for the safety issues, well, it’s a different story. You totally misunderstood me. I am not looking for thrill or adrenaline, trust me, I’m getting much more than I need of those during final exams. I am only doing whatever it takes me to get a good panoramic shot from the above. Once I’m on the edge of a roof, I don’t do backflips or balance hoverboards there. There are a lot of tips and guides in the Internet, do some research, they is very helpful; I am usually following two main rules: there should be always something strong to hold and something not slippery to step on. The rest is good unless you suffer from epilepsy.
There is, of course, peaceful urbex, without any kind of trespassing. For example, the one I did a week ago. When I lived in Roxbury 2.5 years ago (read about my experience in the post from 10 September - 3 December 2013), and went to the university on foot (it was rather a rare experience), I used to pass a wasteland paled with a Rabitz. I thought why would someone pale a wasteland with Rabitz, and why no one was allowed there, but was too lazy to explore. Since all my homework assignments are due at midnight from Sunday to Monday, and I have no weeks on the first day of the week, I decided to go do some exploration. I was having a lunch at International Village (I have some major plans for that building itself, anticipate!), and then decided to take a walk before going to the gym (it is a bad idea to go to the gym right after a good brunch, trust me). That wasteland was right diagonally the Tremont street X Ruggles/Whittier street crossing, in front of Boston Police Headquarters, basically two steps away. The wasteland was very large, and very green, with an abandoned building in the middle (back part of which was not paled with Rabitz, it served as a wall itself: