Some gnarly books, bro
North York Central has a great collection of skateboarding related material. From field manuals for those starting out to anthologies of photographs taken by some of skateboarding's best photographers.
"The skateboarding Field Manual" is a great introduction into the culture of street skateboarding. From setting up your first deck to learning some tricks. This book has loads of photos and skating from many talented skaters and photographers, including some from right here in Toronto. The author, Ryan Stutt, is currently the President/Publisher of, arguably one of Canada's best skatemags, The King Publication - whose headquarters are located in Parkdale.
(Darryl Smith - Ontario Native and Owner of Studio Skateboards - pops a big old shuvit on the Cover of the Skateboarding Field Manual)
TPL has subscriptions to Thrasher magazine - considered the bible of skateboarding - along with a selection of many skate videos.
Finally, if you're looking for a place to skate, the city has some great parks around town. The favorite of many skaters is Dunbat - located just south of the intersection of Dundas and Bathurst - right beside Sanderson Library. Or there is another temporary park setup in Dufferin Grove Park. For more information on skateparks have a look at this link for a more complete list of parks.
There is an endless amount of skate-related content online. Here are just a few of my favorite places to check:
Thrasher Magazine - as earlier stated, its the bible.
Slap Magazine - a former print magazine that has since gone completely digital.
Already Been Done - If you don't know, now you know.
Chrome Ball Incident - Archived skate ads/photos from the 80s and 90s.