You guys realy need to do some research there are a lot of jeep clubs in the GTA. I would start by joining the OF4WD. they will provide ample information and are working to keep the trails open for us. Its only like $30 and well worth the money. They organize and run Camp NL which is probably one of the best organized runs of the year since the jeep jamboree pulled out of Ontario. This is as far as i know the only group that is actually fighting to keep our sport alive. They are working with the government to get our sport acknowledged.
Next check with National 4X4 they have a list of groups that already exist and are well established
Then finally there is a very good local forum that most people in the GTA are on. They have great deals on used stuff and have advertisers specials from Just Jeeps and other local 4x4 shops. There are a lot of local meetings and trail rides that you can join up with.
Oh and if your looking to meet people go checkout the Rubicon Grill in Mississauga. Groups and guys are always there hanging out. The bar is awesome and decorated with jeep stuff and the wings are good too. These guys cater most of the big jeeping events. But you guys just missed the big end of summer bash that the had.