Free Berkeley, CA
Berkeley, across the bay from San Francisco, is notorious for its upper middle class greenwashed yuppies who think Obama is the Jesus of modern Amerika. It also has some good dumpster diving spots and though there is a significant "shop local" thing going on, there are vast department stores and malls (most notably Target and Emery Bay, which technically isn't in Berkeley) that still need to die. Unfortunately, the largely politically uninterested youth really don't care about much besides school, social standing, various extracurricular activities and unlimited texting. Immense Berkeley pride is expressed through use of the word 'hella'.
Berkeley's climate is very nice. It gets a cool breeze from the Bay but it never snows except for in the uppermost parts of the hills, and even there only once every few years. It stays warm for most of the year but rarely goes higher than the low eighties. It has a standard rainy winter starting in October or November, which lasts anywhere from February to May. There is a very long Indian summer.
Free housing, shelters and hostels, etc.
East Bay Food Not Bombs can be found in People's Park, a few blocks off Telegraph, Monday through Friday at about 3 pm.
Planned parenthood, free clinics, free medical advice, Medicare resources, low-cost clinics, etc.
ACLU, free legal aid/counseling, pro bono attorneys, etc.
Armed Forces/Deployment Avoidance Counseling
Legal aid, resources, etc.
There are a lot of beautiful parks in B-Town. Aquatic Park, close to the Marina, has a bitchin' playground and a man-made brackish lake that you can canoe or kayak in (too grimy to swim in). There is also a frisbee course and bike paths and it's easy to get there by bike (just head west on Allston or Bancroft.) It officially closes at sundown. Civic Center Park, by the high school, is the favorite spot for stoner kids (the bicycle cops are everywhere, yet do so little law enforcement). There is always People's Park a block off Telegraph and the Berkeley campus. 
924 Gilman, at Gilman and 8th street, shows free movies most Tuesday nights at 19:00. They also have shows of an assortment of musical styles (also known as punk) every Friday and Saturday night and some Sundays and Thursdays, but they cost 5-12 bucks (usually 7 or 8). However, if you show up an hour or so early, you can get a volunteer job, which means you work half the show and get to watch the rest free!
The local anarchist infoshop is called Long Haul and lives across the street from La Peña and the Starry Plough on Shattuck, in South Berkeley/North Oakland. They have a lot of zines there, and local groups like East Bay Free Skool and Food Not Bombs meet here, plus they have workshops and stuff.
The Slingshot Collective at the Long Haul puts out Slingshot, you can get it free there. There is also the Street Spirit which is given free to homeless folks, who sell it for a buck. You can find people selling it at the farmers markets, on Shattuck, and throughout town.
Any other freebies
Everyone uses BART (Bay Area Rapid Transit) or the buses. Both are kind of expensive now. The attendants at the Bart stations can be really nice and a long explanation can sometimes get them to let you through the side gate for wheelchairs. Bart cards for kids are a little cheaper and though they work in weird ways that are hard to understand, they can allow younger people -- anyone who can pass for 12 -- to ride Bart for slightly less and probably people of any age since nobody checks your Bart card.
Free Clothing and Furniture
Supposedly Urban Outfitters is a good place for snagging stuff.
You can find plenty of free clothing in the Dona Spring Wishing Well, a free box with a long history (30+ years?) full of legal battles. It's on Channing about a half-block West of Grant. Of course it's best to wash the stuff. Clothes, shoes, sometimes even books and CDs can be scored here, needless to say it overflows a lot.
"Wiggling the knob on a gumball machine can fool the machine into thinking you have inserted a coin. Just jam it back and forth several times, fast. This can be very noisy and conspicuous, though: try to find a gumball machine that is out of the way or in a corner, far from cameras and employees (we've noticed this only works on some machines, so look for a store with a wide selection of candy machines and try all of them)."
This works particularly well at the Oakland Ice Center (In Oakland, of course) because most of the candy machines are off out of the way in the little snacks nook and often the employees are busy and there isn't anyone at the snacks counter. Which basically means you can have a candy free-for-all. And there are a shitload of different ones, so try all of them.
Urban Ore, near Ashby and San Pablo, is a good place to get cheap junk of all sorts. Some of the cheapest, most broken stuff is in the far back of the outdoor section, but there is a good deal of worthwhile things inside too. They have started raising their prices, unfortunately.
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