In reply to:
For your first season outdoors, I highly recommend going with some experienced outdoor climbers who can help you make the transition from inside to out as there are many more considerations besides a crag list when you head outside.
For your first season try
Metcalf (top-rope set-ups are easy and guiding is permitted),
Rattlesnake or
Buffalo also have topropes and are close.
Mount Nemo is excellent for sport climbing if you are solid climbing 5.10's or 11's.
Kelso has excellent trad/top rope opportunities too. There are two guidebooks you should own - The Escarpment, and A Sport Climbers Guide to Ontario Limestone (or something like that). They are both available at MEC.
You will need these.
Though the climbing at Lion's Head is spectacular, it is remote and challenging (rappel in, hanging belays). Be sure you have experienced climbers with you who know the area if you want to climb there.