Free Kingston, ONT
Kingston, Canada's first capitol, and hometown of it's first prime minister! To spite this, the place hasn't really grown overly populated, but it's still a nice little town to live, if you don't mind going nowhere in a small town. The city is basically divided in to 4 sections. The west end is by far the biggest, and home to all the new housing developments, big department stores, and frustrating traffic. There's the unnamed area that's halfway between downtown and the west end, it's technically downtown, but it's far enough away from anything significant to not be classified anywhere. There's across the rideau, which is essentially the military base and a few newer developments, and then there's downtown, which itself is divided into 3 sections. There's what is basically the main downtown, where all the stores and city buildings are located, there's the heights (short for rideau heights) which is a lot of lower class wartime housing filled with "at risk" families and drunks, and then there's queens, which is the main campus, and about a 2km radius around it filled with houses that are absolutely beautiful on the outside, but completely destroyed inside due to continuous inhabitance by college students.
There are lots of little places you can spend the night in Kingston. Right down on princess street downtown there's a little section of stores that are "downstairs" being so out of the way, they're all gone out of business and currently just sit there looking crappy. Underneath the staircase is a very good place to spend the night, and as long as you don't make too much ruckus, no one will bother you.
The Alexander Henry Hostel is a nice little place with the added bonus of being on a boat. You can get rooms from $30 a night, but be warned, it's very old, and some rooms can be quite dirty. If you're not really interested in class though, it's a pretty neat place to stay.
on 75 Bader Lane there's the queens backpackers hostels, it costs about $50, not really worth it, but if you really want to its open May-August. 
It's really easy to dine and dash at basically any restaurant downtown, especially if they're really busy. I suggest not doing this at more upscale places though, because they notify police. Martha's table is located at 629 princess, and has meals for anyone who wants one for $1, no proof of poverty required. The hours are here.
There are a few other church run soup kitchens, - a quick search will turn up plenty. Churches also regularly have fundraisers - by serving dinners or breakfasts. These usually range from $10-$30 depending on where its at. The food never disappoints.
Kingston General hospital (KGH) and Hotel Du Hospital are both located downtown, and if you're a citizen it doesn't cost to get checked for things there. There's tons of free counseling about drug use, pregnancy, and other things, but you'll have to do some searching yourself to figure out where to get it.
In the west end (greater Kingston) there's a few beaches around the Invista/Dupont factory on Front Rd. If you go down sunny acres rd (off of front, right next to dupont) there's a nice little public park, with a small beach made of tiny stones. If you keep going down the little path, it goes around the fence (don't worry about the no trespassing sign, everyone does, and security does nothing if they see you) and down farther until you get to a nice flat rocks beach. don't go to the sand beach a little farther on as it's for "S&A club members only", and security will actually kick you out for swimming there.
There's tons of parks in Kingston, if you walk around anywhere you'll find one. In my opinion, the nicest is the one by the waterfront downtown, across from the general hospital, by queens. It stretches quite a ways, but there's always people down there. In the summer Kingston is teaming with shows and performances. Every Wednesday and Sunday July through to the end of August, there's free live shows at the Lion Civic Gardens located next to the Cataraqui Town Centre in the west end. There's also always people putting on shows in confederation park (across from city hall), and just general busking. There are free movies in market square every Thursday night at 7:00 (July) and 8:30 (august), bring your own lawn chair. There's tons of other events that go on, to see them all go to The city's website.
The Ciniplex Odeon movie theatre in the west end is incredibly easy to sneak in to. When there's a really popular movie on, it gets harder, because they make you buy your ticket before getting anywhere, but when there's nothing special, you can just say you're going to the washroom, and then go into the movie. If you have a friend who bought a ticket, you can also get them to open the side door for you. Keep an eye out downtown, especially around Queens, because there's usually events happening. If your looking for free admission, the one's in chalk are usually poor queens students just looking for a good time.
The weather is pretty good, since it's by the lake. In the summer the warmest it gets is usually around 30 Celsius, and in the winter there's about a week in January that it stays at around -30, but after that its usually at -20 or above. There's ALWAYS construction going on in Kingston, and sometimes it can be frustrating, especially "rush hour" but compared to bigger cities, it's nothing, and there's always a way around it. Also, to spite the 5 or so prisons that are located in and around Kingston, it's a pretty safe city, and there's not a lot of major crime to worry about. If you go into some queens campus buildings, there's free newspapers, and local radio stations always have the latest happenings, local and not so.
Library cards cost $5 and never expire, if you like reading go for it. There're tons of shops where you can by pot seeds legally, like 420, the jungle, and smoke signals. Check queens campus for posters about free things, they always have stuff going on for broke ass students, and there's usually nothing saying other people can't take advantage of those deals too. If you're an Ontarian citizen, health care is free, just make sure your health card is updated. (note that health care is free, but if you need prescription drugs, casts, or other things like that, it's not covered).
Buses are super easy to get on to without paying, and if you do choose to pay it costs $2. You also get a transfer ticket for $2 and with it you can basically get across the entire city. Many places have route maps you can pick up, like the Cateraqui town centre information booth. Transfer stations are exceptionally easy to get on the buses, as a lot of times the drivers get out to talk to each other. You can also carry around an expired transfer ticket, and then pretend your just having trouble with the scanner (because this happens a lot too), the driver will usually let you on. If not, it only takes about 2 hours to walk from one end of the city to the other anyways, so its not a big deal.
Free Clothing and Furniture
If you go to kijiji, there's always free furniture and usually some free clothing. You can also snag some nice clothes by going to the mall and just putting things on under your clothes in the change room. Just make sure the girl unlocking the door for you doesn't know how many you brought in. at Liquidation World (LW) you can get clothes for about 50 cents, and cheaper if you go when there's sales. They're nice clothes too.
Get free money by busking. It's legally required that you have a permit, which costs about 15 bucks, but no one ever checks. As long as you don't cause problems, no one's going to bother you. You can also collect beer and wine bottles on Tuesday evenings downtown. Hit up all the apartments, but make sure you get there right after they put them out, because there's other people who do this too. Don't go for the cheap crappy ones, because those people take their own. Go for the expensive looking luxury suits, because those people only drink expensive wine that will get your 20-30 cents a bottle. Beer stores accept everything, wine bottles are usually 20, beer is 10, and cans are 5. It's also easy to get a job, so don't be afraid to apply if you need one.